Contentslib3.dss.go.th/fulltext/c_book/540-549/547.2wanref.pdf · tted in any form or by any pt as...
23
Contents Preface . xxix Acknowledgments . xxxi Autobiography . xxxiii Chemical Abbreviations xxxv PART ONE 1. Abnormal Claisen Rearrangement 1 2. Acetoacetic Ester Condensation 5 3. Acetoacetic Ester Synthesis . 9 4. Acyloin Condensation ................................................. 13 5. Acyloin Rearrangement 18 6. Adkins Catalyst . 21 7. Ainley and King Synthesis ............................................ 25 8. Akabori Amino Acid Reaction . 29 9. Albright-Goldman Oxidation 33 10. Alder Ene Reaction 37 11. Alder-Rickert Reaction ............................................... 41 12. Aldol Reaction and Aldol Condensation 45 v
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19
itle
Contents
Preface xxix
Acknowledgments xxxi
Autobiography xxxiii
Chemical Abbreviations xxxv
PART ONE
1 Abnormal Claisen Rearrangement 1
2 Acetoacetic Ester Condensation 5
3 Acetoacetic Ester Synthesis 9
4 Acyloin Condensation 13
5 Acyloin Rearrangement 18
6 Adkins Catalyst 21
7 Ainley and King Synthesis 25
8 Akabori Amino Acid Reaction 29
9 Albright-Goldman Oxidation 33
10 Alder Ene Reaction 37
11 Alder-Rickert Reaction 41
12 Aldol Reaction and Aldol Condensation 45
v
Administrator
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Ref5472 WAN V1
vi CONTENTS
13 Algar-Flynn-Oyamada (AFO) Reaction 52
14 Alkene Metathesis 57
15 Allan-Robinson Condensation 64
16 Allylic Rearrangement 68
17 Amadori Rearrangement 74
18 Andrussow Process 80
19 Angeli-Remini Reaction 83
20 ANRORC Rearrangement 87
21 Anschutz Anthracene Synthesis 91
22 Appel Reaction 95
23 Arens-van Dorp Reaction bull 100
24 Arndt-Eistert Synthesis 103
25 Asinger Reaction 107
26 Aston-Greenburg Rearrangement 111
27 Atherton-Todd Reaction 114
28 Auwers-Skita Rule 119
29 Aza-Claisen Rearrangement 123
30 Baddeley Isomerization 128
31 Baeyer Diarylmethane Synthesis 132
32 Baeyer-Drewson Reaction 136
33 Baeyer Indole Synthesis 140
34 Baeyer Oxindole Synthesis 144
35 Baeyer Pyridine Synthesis 147
36 Baeyer-Villiger Oxidation 150
37 Bailey Peptide Synthesis 156
38 Bakelite Process 160
39 Baker-Ollis Sydnones Synthesis 164
40 Baker- Venkataraman Rearrangement 168
41 Ball-Goodwin-Morton Oxidation 173
42 Bally-Scholl Reaction 176
43 Balsohn Alkylation 181
44 Balz-Schiemann Reaction 185
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57
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middot 123
128
132
136
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middot 160
164
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middot 176
middot 181
185
CONTENTS vii
45 Bamberger Rearrangement 191
46 Bamford-Stevens Reaction 195
47 Barbier Reaction 202
48 Barbier-Wieland Degradation 210
49 Bardhan Sengupta Synthesis 215
50 Bargellini Condensation 220
51 Bart Reaction 224
52 Bartoli Indole Synthesis 228
53 Barton Decarboxylation 232
54 Barton Deoxygenation 237
55 Barton Reaction 245
56 Barton-Kellogg Olefination 249
57 Barton-Zard Pyrrole Synthesis 254
58 Batcho-Leimgruber Indole Synthesis 258
59 Baudisch Reaction 263
60 Baumann-Fromm Thiophene Synthesis 267
61 Baumgarten a-Amino Ketone Synthesis 271
62 Baylis-Hillman Reaction 275
63 Bechamp Reduction 284
64 Beckmann Rearrangement and Beckmann Fragmentation 288
65 Bedoukian Halogenation 296
66 Behal-Sommelet Rearrangement 300
67 Beirut Reaction 303
68 Bellus-Claisen Rearrangement 307
69 Benary Reaction 311
70 Benkeser Reduction 315
71 Benzidine Rearrangement 320
72 Benzilic Acid Rearrangement 326
73 Benzoin Condensation 331
74 Bergius Process 337
75 Bergman Cyclization 341
76 Bergmann Degradation 349
viii CONTENTS
77 Bergmann-Stern Azlactone Synthesis 353
78 Bergmann-Zervas Peptide Synthesis 358
79 Bernthsen Reaction 362
80 Berti Olefination 366
81 Bertram-Walbaum Reaction 370
82 Betti Reaction 374
83 Biginelli Reaction 379
84 Birch Reduction 387
85 Birckenbach-Goubeau Halogenation 398
86 Birnbaum-Simonini Reaction 402
87 Bischler Reaction 406
88 Bischler-Napieralski Isoquinoline Synthesis 410
89 Black Rearrangement 416
90 Blaise Ketone Synthesis 420
91 Blaise Reaction 424
92 Blanc Chloromethylation 429
93 Blanc Rule 433
94 Blomquist Cyclic Ketone Synthesis 437
95 Bobbitt Reaction 441
96 Bodroux Amide Synthesis 445
97 Bodroux-Chichibabin Reaction 448
98 Boeseken Oxidation 452
99 Bogert-Cook Synthesis 455
100 Bohn-Schmidt Reaction 459
101 Boord Olefin Synthesis 463
102 Borsche-Berkhout Reaction 468
103 Borsche-Drechsel Reaction 471
104 Borsche-Koelsch Cinnoline Synthesis 474
105 Bougault Reaction 478
106 Boulton-Katritzky Rearrangement 482
107 Bourgel Alkyne Synthesis 487
108 Bouveault Aldehyde Synthesis 490
gt
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362
366
370
- 374
379
387
398
402
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416
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433
437
441
445
448
452
455
459
463
468
471
474
478
482
487
490
CONTENTS ix
109 Bouveault-Blanc Reduction 493
110 Boyland-Sims Oxidation 497
111 Bradsher Cyclization 501
112 Bradsher Cycloaddition 506
113 Bradsher Pyridinium Salt Synthesis 511
114 Brandi-Guarna Reaction 515
115 Breckpot p-Lactam Synthesis 521
116 Bredts Rule 525
117 Brook Rearrangement 529
118 Brown Hydroboration 536
119 Bruckner Isoquinoline Synthesis 544
120 Bucherer Carbazole Synthesis 549
121 Bucherer Reaction 553
122 Bucherer-Bergs Hydantoin Synthesis 557
123 Buchner Ring Expansion 562
124 Biichner-Curtlus-Schlotterbeck Reaction 567
125 Buchwald Indoline Synthesis 570
126 Buchwald-Hartwig Amination 575
127 Burton Triftuoromethylation 582
128 Cadogan-Sundberg Indole Synthesis 585
129 Caglioti Reaction 589
130 Cahours-Hofmann Reaction 595
131 Camps Reaction 598
132 Cannizzaro Reaction 602
133 Carboni-Lindsey Reaction 606
134 Carroll Rearrangement 611
135 Castro Indole Synthesis 616
136 Castro-Stephens Coupling 619
137 Chan Rearrangement 624
138 Chapman Rearrangement 627
139 Chichibabin Amination 631
140 Chichibabin Pyridine Synthesis 635
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
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709
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717
722
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734
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761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
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CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
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CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
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1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
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2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
vi CONTENTS
13 Algar-Flynn-Oyamada (AFO) Reaction 52
14 Alkene Metathesis 57
15 Allan-Robinson Condensation 64
16 Allylic Rearrangement 68
17 Amadori Rearrangement 74
18 Andrussow Process 80
19 Angeli-Remini Reaction 83
20 ANRORC Rearrangement 87
21 Anschutz Anthracene Synthesis 91
22 Appel Reaction 95
23 Arens-van Dorp Reaction bull 100
24 Arndt-Eistert Synthesis 103
25 Asinger Reaction 107
26 Aston-Greenburg Rearrangement 111
27 Atherton-Todd Reaction 114
28 Auwers-Skita Rule 119
29 Aza-Claisen Rearrangement 123
30 Baddeley Isomerization 128
31 Baeyer Diarylmethane Synthesis 132
32 Baeyer-Drewson Reaction 136
33 Baeyer Indole Synthesis 140
34 Baeyer Oxindole Synthesis 144
35 Baeyer Pyridine Synthesis 147
36 Baeyer-Villiger Oxidation 150
37 Bailey Peptide Synthesis 156
38 Bakelite Process 160
39 Baker-Ollis Sydnones Synthesis 164
40 Baker- Venkataraman Rearrangement 168
41 Ball-Goodwin-Morton Oxidation 173
42 Bally-Scholl Reaction 176
43 Balsohn Alkylation 181
44 Balz-Schiemann Reaction 185
I
bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
52
57
64
68
74
80
83
87
91
95
100
103
107
111
114
119
middot 123
128
132
136
140
144
147
150
156
middot 160
164
168
173
middot 176
middot 181
185
CONTENTS vii
45 Bamberger Rearrangement 191
46 Bamford-Stevens Reaction 195
47 Barbier Reaction 202
48 Barbier-Wieland Degradation 210
49 Bardhan Sengupta Synthesis 215
50 Bargellini Condensation 220
51 Bart Reaction 224
52 Bartoli Indole Synthesis 228
53 Barton Decarboxylation 232
54 Barton Deoxygenation 237
55 Barton Reaction 245
56 Barton-Kellogg Olefination 249
57 Barton-Zard Pyrrole Synthesis 254
58 Batcho-Leimgruber Indole Synthesis 258
59 Baudisch Reaction 263
60 Baumann-Fromm Thiophene Synthesis 267
61 Baumgarten a-Amino Ketone Synthesis 271
62 Baylis-Hillman Reaction 275
63 Bechamp Reduction 284
64 Beckmann Rearrangement and Beckmann Fragmentation 288
65 Bedoukian Halogenation 296
66 Behal-Sommelet Rearrangement 300
67 Beirut Reaction 303
68 Bellus-Claisen Rearrangement 307
69 Benary Reaction 311
70 Benkeser Reduction 315
71 Benzidine Rearrangement 320
72 Benzilic Acid Rearrangement 326
73 Benzoin Condensation 331
74 Bergius Process 337
75 Bergman Cyclization 341
76 Bergmann Degradation 349
viii CONTENTS
77 Bergmann-Stern Azlactone Synthesis 353
78 Bergmann-Zervas Peptide Synthesis 358
79 Bernthsen Reaction 362
80 Berti Olefination 366
81 Bertram-Walbaum Reaction 370
82 Betti Reaction 374
83 Biginelli Reaction 379
84 Birch Reduction 387
85 Birckenbach-Goubeau Halogenation 398
86 Birnbaum-Simonini Reaction 402
87 Bischler Reaction 406
88 Bischler-Napieralski Isoquinoline Synthesis 410
89 Black Rearrangement 416
90 Blaise Ketone Synthesis 420
91 Blaise Reaction 424
92 Blanc Chloromethylation 429
93 Blanc Rule 433
94 Blomquist Cyclic Ketone Synthesis 437
95 Bobbitt Reaction 441
96 Bodroux Amide Synthesis 445
97 Bodroux-Chichibabin Reaction 448
98 Boeseken Oxidation 452
99 Bogert-Cook Synthesis 455
100 Bohn-Schmidt Reaction 459
101 Boord Olefin Synthesis 463
102 Borsche-Berkhout Reaction 468
103 Borsche-Drechsel Reaction 471
104 Borsche-Koelsch Cinnoline Synthesis 474
105 Bougault Reaction 478
106 Boulton-Katritzky Rearrangement 482
107 Bourgel Alkyne Synthesis 487
108 Bouveault Aldehyde Synthesis 490
gt
bullbullbullbullbullbullbullbullbullbullbullbullbullbull
353
358
362
366
370
- 374
379
387
398
402
406
410
416
420
424
429
433
437
441
445
448
452
455
459
463
468
471
474
478
482
487
490
CONTENTS ix
109 Bouveault-Blanc Reduction 493
110 Boyland-Sims Oxidation 497
111 Bradsher Cyclization 501
112 Bradsher Cycloaddition 506
113 Bradsher Pyridinium Salt Synthesis 511
114 Brandi-Guarna Reaction 515
115 Breckpot p-Lactam Synthesis 521
116 Bredts Rule 525
117 Brook Rearrangement 529
118 Brown Hydroboration 536
119 Bruckner Isoquinoline Synthesis 544
120 Bucherer Carbazole Synthesis 549
121 Bucherer Reaction 553
122 Bucherer-Bergs Hydantoin Synthesis 557
123 Buchner Ring Expansion 562
124 Biichner-Curtlus-Schlotterbeck Reaction 567
125 Buchwald Indoline Synthesis 570
126 Buchwald-Hartwig Amination 575
127 Burton Triftuoromethylation 582
128 Cadogan-Sundberg Indole Synthesis 585
129 Caglioti Reaction 589
130 Cahours-Hofmann Reaction 595
131 Camps Reaction 598
132 Cannizzaro Reaction 602
133 Carboni-Lindsey Reaction 606
134 Carroll Rearrangement 611
135 Castro Indole Synthesis 616
136 Castro-Stephens Coupling 619
137 Chan Rearrangement 624
138 Chapman Rearrangement 627
139 Chichibabin Amination 631
140 Chichibabin Pyridine Synthesis 635
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I
bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
52
57
64
68
74
80
83
87
91
95
100
103
107
111
114
119
middot 123
128
132
136
140
144
147
150
156
middot 160
164
168
173
middot 176
middot 181
185
CONTENTS vii
45 Bamberger Rearrangement 191
46 Bamford-Stevens Reaction 195
47 Barbier Reaction 202
48 Barbier-Wieland Degradation 210
49 Bardhan Sengupta Synthesis 215
50 Bargellini Condensation 220
51 Bart Reaction 224
52 Bartoli Indole Synthesis 228
53 Barton Decarboxylation 232
54 Barton Deoxygenation 237
55 Barton Reaction 245
56 Barton-Kellogg Olefination 249
57 Barton-Zard Pyrrole Synthesis 254
58 Batcho-Leimgruber Indole Synthesis 258
59 Baudisch Reaction 263
60 Baumann-Fromm Thiophene Synthesis 267
61 Baumgarten a-Amino Ketone Synthesis 271
62 Baylis-Hillman Reaction 275
63 Bechamp Reduction 284
64 Beckmann Rearrangement and Beckmann Fragmentation 288
65 Bedoukian Halogenation 296
66 Behal-Sommelet Rearrangement 300
67 Beirut Reaction 303
68 Bellus-Claisen Rearrangement 307
69 Benary Reaction 311
70 Benkeser Reduction 315
71 Benzidine Rearrangement 320
72 Benzilic Acid Rearrangement 326
73 Benzoin Condensation 331
74 Bergius Process 337
75 Bergman Cyclization 341
76 Bergmann Degradation 349
viii CONTENTS
77 Bergmann-Stern Azlactone Synthesis 353
78 Bergmann-Zervas Peptide Synthesis 358
79 Bernthsen Reaction 362
80 Berti Olefination 366
81 Bertram-Walbaum Reaction 370
82 Betti Reaction 374
83 Biginelli Reaction 379
84 Birch Reduction 387
85 Birckenbach-Goubeau Halogenation 398
86 Birnbaum-Simonini Reaction 402
87 Bischler Reaction 406
88 Bischler-Napieralski Isoquinoline Synthesis 410
89 Black Rearrangement 416
90 Blaise Ketone Synthesis 420
91 Blaise Reaction 424
92 Blanc Chloromethylation 429
93 Blanc Rule 433
94 Blomquist Cyclic Ketone Synthesis 437
95 Bobbitt Reaction 441
96 Bodroux Amide Synthesis 445
97 Bodroux-Chichibabin Reaction 448
98 Boeseken Oxidation 452
99 Bogert-Cook Synthesis 455
100 Bohn-Schmidt Reaction 459
101 Boord Olefin Synthesis 463
102 Borsche-Berkhout Reaction 468
103 Borsche-Drechsel Reaction 471
104 Borsche-Koelsch Cinnoline Synthesis 474
105 Bougault Reaction 478
106 Boulton-Katritzky Rearrangement 482
107 Bourgel Alkyne Synthesis 487
108 Bouveault Aldehyde Synthesis 490
gt
bullbullbullbullbullbullbullbullbullbullbullbullbullbull
353
358
362
366
370
- 374
379
387
398
402
406
410
416
420
424
429
433
437
441
445
448
452
455
459
463
468
471
474
478
482
487
490
CONTENTS ix
109 Bouveault-Blanc Reduction 493
110 Boyland-Sims Oxidation 497
111 Bradsher Cyclization 501
112 Bradsher Cycloaddition 506
113 Bradsher Pyridinium Salt Synthesis 511
114 Brandi-Guarna Reaction 515
115 Breckpot p-Lactam Synthesis 521
116 Bredts Rule 525
117 Brook Rearrangement 529
118 Brown Hydroboration 536
119 Bruckner Isoquinoline Synthesis 544
120 Bucherer Carbazole Synthesis 549
121 Bucherer Reaction 553
122 Bucherer-Bergs Hydantoin Synthesis 557
123 Buchner Ring Expansion 562
124 Biichner-Curtlus-Schlotterbeck Reaction 567
125 Buchwald Indoline Synthesis 570
126 Buchwald-Hartwig Amination 575
127 Burton Triftuoromethylation 582
128 Cadogan-Sundberg Indole Synthesis 585
129 Caglioti Reaction 589
130 Cahours-Hofmann Reaction 595
131 Camps Reaction 598
132 Cannizzaro Reaction 602
133 Carboni-Lindsey Reaction 606
134 Carroll Rearrangement 611
135 Castro Indole Synthesis 616
136 Castro-Stephens Coupling 619
137 Chan Rearrangement 624
138 Chapman Rearrangement 627
139 Chichibabin Amination 631
140 Chichibabin Pyridine Synthesis 635
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
viii CONTENTS
77 Bergmann-Stern Azlactone Synthesis 353
78 Bergmann-Zervas Peptide Synthesis 358
79 Bernthsen Reaction 362
80 Berti Olefination 366
81 Bertram-Walbaum Reaction 370
82 Betti Reaction 374
83 Biginelli Reaction 379
84 Birch Reduction 387
85 Birckenbach-Goubeau Halogenation 398
86 Birnbaum-Simonini Reaction 402
87 Bischler Reaction 406
88 Bischler-Napieralski Isoquinoline Synthesis 410
89 Black Rearrangement 416
90 Blaise Ketone Synthesis 420
91 Blaise Reaction 424
92 Blanc Chloromethylation 429
93 Blanc Rule 433
94 Blomquist Cyclic Ketone Synthesis 437
95 Bobbitt Reaction 441
96 Bodroux Amide Synthesis 445
97 Bodroux-Chichibabin Reaction 448
98 Boeseken Oxidation 452
99 Bogert-Cook Synthesis 455
100 Bohn-Schmidt Reaction 459
101 Boord Olefin Synthesis 463
102 Borsche-Berkhout Reaction 468
103 Borsche-Drechsel Reaction 471
104 Borsche-Koelsch Cinnoline Synthesis 474
105 Bougault Reaction 478
106 Boulton-Katritzky Rearrangement 482
107 Bourgel Alkyne Synthesis 487
108 Bouveault Aldehyde Synthesis 490
gt
bullbullbullbullbullbullbullbullbullbullbullbullbullbull
353
358
362
366
370
- 374
379
387
398
402
406
410
416
420
424
429
433
437
441
445
448
452
455
459
463
468
471
474
478
482
487
490
CONTENTS ix
109 Bouveault-Blanc Reduction 493
110 Boyland-Sims Oxidation 497
111 Bradsher Cyclization 501
112 Bradsher Cycloaddition 506
113 Bradsher Pyridinium Salt Synthesis 511
114 Brandi-Guarna Reaction 515
115 Breckpot p-Lactam Synthesis 521
116 Bredts Rule 525
117 Brook Rearrangement 529
118 Brown Hydroboration 536
119 Bruckner Isoquinoline Synthesis 544
120 Bucherer Carbazole Synthesis 549
121 Bucherer Reaction 553
122 Bucherer-Bergs Hydantoin Synthesis 557
123 Buchner Ring Expansion 562
124 Biichner-Curtlus-Schlotterbeck Reaction 567
125 Buchwald Indoline Synthesis 570
126 Buchwald-Hartwig Amination 575
127 Burton Triftuoromethylation 582
128 Cadogan-Sundberg Indole Synthesis 585
129 Caglioti Reaction 589
130 Cahours-Hofmann Reaction 595
131 Camps Reaction 598
132 Cannizzaro Reaction 602
133 Carboni-Lindsey Reaction 606
134 Carroll Rearrangement 611
135 Castro Indole Synthesis 616
136 Castro-Stephens Coupling 619
137 Chan Rearrangement 624
138 Chapman Rearrangement 627
139 Chichibabin Amination 631
140 Chichibabin Pyridine Synthesis 635
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
gt
bullbullbullbullbullbullbullbullbullbullbullbullbullbull
353
358
362
366
370
- 374
379
387
398
402
406
410
416
420
424
429
433
437
441
445
448
452
455
459
463
468
471
474
478
482
487
490
CONTENTS ix
109 Bouveault-Blanc Reduction 493
110 Boyland-Sims Oxidation 497
111 Bradsher Cyclization 501
112 Bradsher Cycloaddition 506
113 Bradsher Pyridinium Salt Synthesis 511
114 Brandi-Guarna Reaction 515
115 Breckpot p-Lactam Synthesis 521
116 Bredts Rule 525
117 Brook Rearrangement 529
118 Brown Hydroboration 536
119 Bruckner Isoquinoline Synthesis 544
120 Bucherer Carbazole Synthesis 549
121 Bucherer Reaction 553
122 Bucherer-Bergs Hydantoin Synthesis 557
123 Buchner Ring Expansion 562
124 Biichner-Curtlus-Schlotterbeck Reaction 567
125 Buchwald Indoline Synthesis 570
126 Buchwald-Hartwig Amination 575
127 Burton Triftuoromethylation 582
128 Cadogan-Sundberg Indole Synthesis 585
129 Caglioti Reaction 589
130 Cahours-Hofmann Reaction 595
131 Camps Reaction 598
132 Cannizzaro Reaction 602
133 Carboni-Lindsey Reaction 606
134 Carroll Rearrangement 611
135 Castro Indole Synthesis 616
136 Castro-Stephens Coupling 619
137 Chan Rearrangement 624
138 Chapman Rearrangement 627
139 Chichibabin Amination 631
140 Chichibabin Pyridine Synthesis 635
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
X CONTENTS
141 Chretien-Longi Reaction 639
142 Chugaev Reaction 642
143 Ciamician-Dennstedt Reaction 646
144 Claisen Rearrangement 649
145 Claisen-Schmidt Condensation 660
146 Clauson-Kaas Reaction 665
147 Clay-Kinnear-Perren Condensation 669
148 Clayton-Jensen Chlorophosphonation 673
149 Clemmensen Reduction 677
150 Cohen Reductive Lithiation 683
151 Combes Quinoline Synthesis 688
152 Conrad-Limpach Quinoline Synthesis 692
153 Cope Elimination 697
154 Cope Rearrangement 702
155 Corey-Bakshi-Shibata Reduction 709
156 Corey-Chaykovsky Epoxidation 713
157 Corey-Fuchs Reaction 717
158 Corey-Gilman-Ganem Oxidation 722
159 Corey-Kim Oxidation 726
160 Corey-Kwiatkowski Reaction 730
161 Corey-Link Reaction 734
162 Corey-Schmidt Oxidation 738
163 Corey-Suggs Oxidation 742
164 Corey-Winter Olefination 746
165 Cornforth Rearrangement 750
166 Craig 2-Bromo-Pyridine Synthesis 753
167 Crams Rule 756
168 Criegee Glycol Oxidation 761
169 Criegee Ozonolysis 765
170 Criegee Rearrangement 770
171 Crum-Brown-Gibson Substitution Rule 775
172 Curtius Rearrangement 780
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I
1
bullbullbullbullbullbullbullbullbullbullbullbullbullbull 639
642
646
-bullbullbullbullbullbullbullbullbullbullbullbullbull 649
660
665
669
673
677
683
688
692
697
702
709
713
717
722
726
730
734
738
742
746
750
753
756
761
765
770
775
780
CONTENTS xi
786173 [m+n(+bullbullbull )] Cycloaddition
174 [2+2] Cycloaddition 819
175 Dakin Reaction 829
176 Dakin-West Reaction 832
177 Danheiser Annulation 837
178 Darzens Condensation 841
179 Darzens Halogenation 846
180 Darzens Olefin Acylation 848
181 Darzens-Nenitzescu Reaction 851
182 Davidson Oxazole Cyclization 855
183 de Mayo Reaction 858
184 Decker-Becker Secondary Amine Synthesis 862
185 Delepine Reaction 865
186 Demjanov Rearrangement 868
187 Dess-Martin Periodinane Oxidation 871
188 D-Homo Rearrangement 877
189 Dieckmann Condensation 881
190 Diels-Alder Reaction 886
191 Diels-Reese Reaction 892
192 Dienol-Benzene Rearrangement 897
193 Dienone-Phenol Rearrangement 900
194 Dimroth Rearrangement 905
195 Dimiddotn-Methane Rearrangement 910
196 13middotDipo)ar Cycloaddition 916
197 Doebner Reaction 921
198 Doebner-Miller Reaction 924
199 Doering-Moore-Skattebel Reaction 930
200 Dotz Benzannulation 934
201 Dowd-Beckwith Ring Expansion 939
202 Duff Reaction 942
203 Dutt- Wormall Reaction 946
204 Eastwood Olefination 949
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xii CONTENTS
205 Eder Reaction 952
206 Edman Degradation 954
207 Eglinton Coupling 959
208 Ehrlich-Sachs Reaction 964
209 Einhorn Acylation 967
210 Einhorn-Brunner Reaction 971
211 Eisleb Alkylation 974
212 Elbs Persulfate Oxidation 977
213 Elbs Reaction 982
214 Eltekoff Hydrolysis 986
215 Emde Degradation 989
216 Emmert Reaction 993
217 Erlenmeyer-Plochl Azlactone Synthesis 997
218 Eschenmoser Coupling 1001
219 Eschenmoser Fragmentation 1005
220 Eschweiler-Clarke Methylation 1009
221 Ester Pyrolysis 1013
222 Etard Reaction 1017
223 Evans Aldol Reaction 1021
224 Favorskii Rearrangement 1026
225 Favorskii-Babayan Reaction 1032
226 Feist-Benary Reaction 1036
227 Fenton Reaction 1041
228 Ferrier Reaction 1046
229 Ferrier-II Rearrangement 1051
230 Fetizon Oxidation 1055
231 Finkelstein Reaction 1060
232 Fischer Carbene Complexes 1064
233 Fischer Indole Synthesis 1069
234 Fischer Oxazole Synthesis 1076
235 Fischer Phenylhydrazine Synthesis 1080
236 Fischer Phenylhydrazone and Osazone Synthesis 1083
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
CONTENTS xiii
952bull bullbullbullbullbullbullbullbullbullbullbull 10 bullbull 237 Fischer-Helferich Glycosylation bullbullbull 1088
middot 954 238 Fischer-Hepp Rearrangement 1091
959bull bullbullbullbullbullbullbullbullbull 10 bullbull 10 bull 239 Fischer-Speier Esterification 1095
middot 964 240 Fischer- Tropsch Synthesis 1098
bullbullbullbullbullbullbullbullbullbullbullbull 10 bullbull 241 Fleming- Tamao Oxidation 1103967
971 242 Flood Reaction 1107
243 Forster Reaction 1110 974
bullbullbullbullbullbullbullbullbull 10 bullbullbullbullbull 977 244 Franchimont Condensation 1113
982 245 Frankland Reaction 1116
986bullbullbullbullbullbullbullbullbullbullbullbullbull 10 bull 246 Frater-Seebach Alkylation 1120
989 247 Freund Reaction 1123
993bullbullbullbullbull 10 bullbullbullbullbull 1010 10 248 Friedel-Crafts Acylation 1126
bullbullbullbullbull 10 bullbullbull 10 bullbullbullbullbull 249 Friedel-Crafts Alkylation 1131997
1001 250 Friedlander Condensation 1137
bullbullbullbull 1010 bullbullbullbullbullbull 1005 251 Fries Rearrangement 1143
1009 252 Frltsch-Buttenberg-Wiechell Rearrangement 1151
1013 253 Fujimoto-Belleau Reaction 1155
1017 254 Fukuyama Amine Synthesis 1159
1021 255 Fukuyama Indole Synthesis 1164
1026 256 Fiirstner Indole Synthesis 1170
1032 257 Gabriel Primary Amine Synthesis 1176
1036 258 Gabriel Reaction 1180
bullbullbullbullbullbullbullbullbull 10 bullbullbullbull 1041 259 Gabriel-Colman Rearrangement 1183
1046 260 Garner Aldehyde 1187
1051 261 Gassman Indole Synthesis 1191
1055 262 Gassman Oxindole Synthesis 1194
1060 263 Gassman Reaction 1198
1064 264 Gattermann Aldehyde Synthesis 1202
1069 265 Gattermann Reaction 1206
1076 266 Gattermann-Koch Formylation 1209
1080 267 Gewald Reaction 1213
1083 268 Ghosez Cyclization 1217
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xiv CONTENTS
269 Ghosez Keteniminium-Olefin Cyclization 1221
270 Gibbs-Wohl Naphthalene Oxidation 1227
271 Gilman-Cason Ketone Synthesis 1230
272 Gilman-Speeter Reaction 1234
273 Gomberg Free Radical Reaction 1238
274 Gomberg-Bachmann Pinacol Synthesis 1245
275 Gomberg-Bachmann Reaction 1248
276 Gould-Jacobs Reaction 1252
277 Graebe-Ullmann Synthesis 1256
278 Granacher Synthesis 1260
279 Gribble Reductive Amination 1264
280 Griess Diazotization 1267
281 Grignard Degradation 1271
282 Grignard Reaction 1273
283 Grob Fragmentation 1279
284 Grosheintz-Fischer-Reissert Aldehyde Synthesis 1284
285 Grundmann Aldehyde Synthesis 1288
286 Gryszkiewicz- Trochimowski and Mccombie Fluorination 1291
287 Guareschi Reaction 1294
288 Guerbet Condensation 1298
289 Gutknecht Condensation 1302
PART TWO
290 Hajos-Parrish-Eder-Sauer-Wiechert Reaction 1305
291 Haller-Bauer Cleavage 1310
292 Hammick Reaction 1314
293 Hansley-Prelog Acyloin Condensation 1317
294 Hantzsch Dihydropyridine Synthesis 1321
295 Hantzsch Pyrrole Synthesis 1326
296 Hantzsch Thiazole Synthesis 1330
297 Hass-Bender Oxidation 1335
298 Haworth Methylation 1338
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I bullbullbullbullbullbullbullbullbullbullbullbullbull
I
middot 1221
1227
1230
1234
1238
1245
1248
1252
1256
1260
1264
1267
1271
1273
1279
1284
1288
bullbullbullbullbullbullbullbullbullbullbull 1291
1294
1298
1302
1305
1310
1314
1317
1321
1326
1330
1335
1338
CONTENTS XV
299 Haworth Synthesis 1342
300 Hayashi Rearrangement 1347
301 Heck Reaction 1350
302 Hegedus Indole Synthesis 1358
303 Helferich Condensation 1363
304 Helferich Glycosylation 1367
305 Hell-Volhard-Zelinsky Reaction 1371
306 Hemetsberger Indole Synthesis 1375
307 Henkel Reaction 1379
308 Henry Reaction 1383
309 Herbst-Engel Transamination 1388
310 Heron Rearrangement 1392
311 Herz Reaction 1395
312 Heumann Indigo Process 1399
313 Heyns Rearrangement 1403
314 Hilbert-Johnson Reaction 1408
315 Hinsberg Oxindole Synthesis 1415
316 Hinsberg Reaction 1418
317 Hinsberg Sulfone Synthesis 1422
318 Hinsberg Thiophene Synthesis 1426
319 Hiyama Coupling 1430
320 Hoch-Campbell Reaction 1434
321 Hock Rearrangement 1438
322 Hofer-Moest Reaction 1443
323 Hofmann Degradation 1447
324 Hofmann Elimination 1451
325 Hofmann Isonitrile Synthesis 1457
326 Hofmann Rule 1460
327 Hofrnann-Lotfler-Freytag Reaction 1464
328 Hofmann-Martius Rearrangement 1469
329 Hofmann-Sand Reaction 1473
330 Hooker Oxidation 1477
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xvi CONTENTS
331 Horensteln-Pahlicke Reaction 1481
332 Horner-Wadsworth-Emmons Olefination bull 1484
333 Hosomi-Sakurai Allylation 1491
334 Houhen-Hoesch Reaction 1496
335 Houdry Cracking Process 1501
336 Huisgen Pyrrole Synthesis 1504
337 Hunsdiecker Condensation 1508
338 Hunsdiecker Reaction 1511
339 Hydroformylation 1516
340 Iodolactonization 1521
341 Irvine-Purdie Methylation 1526
342 Jacobsen Rearrangement 1530
343 Jacobsen-Katsuki Epoxidation 1534
344 Janovsky Reaction 1542
345 Japp-Klingemann Fischer Indole Synthesis 1547
346 Japp-Klingemann Reaction 1552
347 Japp-Maitland Condensation 1558
348 Johnson Orthoester Claisen Rearrangement 1561
349 Jones Oxidation 1564
350 Jourdan-Ullmann Reaction 1569
351 Julia Olefination 1576
352 Julia-Colonna Asymmetric Epoxidation 1583
353 Kabachnik-Fields Reaction 1588
354 Kahne Glycosylation 1593
355 Keck Allylation 1597
356 Keck Macrolactonization 1601
357 Kemp Elimination 1605
358 Kennedy Oxidative Cyclization 1609
359 Kiliani-Fischer Cyanohydrin Synthesis 1613
360 Kishner Decomposition 1617
361 Knoevenagel Condensation 1621
362 Knoevenagel Diazotization Method 1627
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 1481
1484
1491
1496
1501
1504
1508
1511
1516
1521
1526
1530
1534
1542
1547
1552
1558
1561
1564
1569
1576
1583
1588
1593
1597
1601
1605
1609
1613
1617
1621
1627
CONTENTS xvii
363 Knorr Pyrazole Synthesis 1631
364 Knorr Pyrrole Synthesis 1634
365 Knorr Quinoline Synthesis 1638
366 Koch-Haaf Carboxylation 1642
367 Kochi Reaction 1646
368 Koenigs-Knorr Reaction 1650
369 Kolbe Electrolysis 1656
370 Kolbe Nitrile Synthesis 1661
371 Kolbe-Schmidt Reaction 1664
372 Kondrateva Pyridine Synthesis 1668
373 Kornblum Oxidation 1672
374 Kornblum-Delamare Rearrangement 1675
375 Kostanecki-Robinson Reaction 1679
376 Kowalski Ester Homologation 1683
377 Krapcho Decarboxylation 1687
378 Kriewitz Condensation 1692
379 Krohnke Pyridine Synthesis 1695
380 Kuhn-Roth Oxidation 1699
381 Kuhn-Winterstein Reduction 1703
382 Kulinkovich Cyclopropanation 1706
383 KutscherofT Acetylene Hydration 1710
384 Lander Rearrangement 1713
385 Larock Indole Synthesis 1717
386 Lawessons Reagent 1722
387 Lebedev Process 1728
388 Lehmstedt-Tanasescu Reaction 1731
389 Lemieux-Johnson Oxidation 1734
390 Leuckart Reaction 1737
391 Leuckart Thiophenol Synthesis 1743
392 Levinstein Process 1747
393 Lieben Iodoform Reaction 1750
394 Liebeskind-Srogl Cross-Coupling 1754
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xviii CONTENTS
395 Lindlar Hydrogenation 1758
396 Lobry de Bruyn-Alberda van Ekenstein Transformation 1763
397 Lombardo Methylenation 1767
398 Lossen Rearrangement 1772
399 Luche Reaction 1777
400 Luche Reduction 1782
401 MacDonald-Fischer Degradation 1787
402 Madelung Indole Synthesis 1791
403 Maillard Reaction 1795
404 Maitland-Japp Reaction 1800
405 Majetich Annulation 1803
406 Malaprade Reaction 1807
407 Malonic Ester Synthesis 1811
408 Mandelic Acid Synthesis 1816
409 Mannich Reaction 1820
410 Marckwald Asymmetric Synthesis 1829
411 Markownikoff Rule and Anti-Markownikoff Rule 1833
412 Martinet Reaction 1838
413 Martins Sulfurane 1841
414 Mattox-Kendall Reaction 1845
415 McCormack Cycloaddition 1849
416 McFadyen-Stevens Reaction 1853
417 McLafferty Rearrangement 1856
418 McMurry Coupling 1860
419 Meerwein Arylation 1866
420 Meerwein-Ponndorf-Verley Reduction 1871
421 Meerweins Salt 1877
422 Meinwald Rearrangement 1880
423 Meisenheimer Complexes 1883
424 Meisenheimer Rearrangement 1889
425 Menke Nitration 1893
426 Menschutkin Reaction 1897
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I
I
bullbullbullbullbullbullbullbullbullbullbullbullbull
bullbullbullbullbullbullbullbullbullbullbullbullbull
1758
1763
1767
1772
1777
1782
1787
1791
1795
1800
1803
1807
1811
1816
1820
1829
1833
1838
1841
1845
1849
1853
1856
1860
1866
1871
1877
1880
1883
1889
1893
1897
CONTENTS xix
427 Mentzer Pyrone Synthesis 1901
428 Merrifield Solid-Phase Peptide Synthesis 1905
429 Meyer-Hartmann Reaction 1910
430 Meyers Aldehyde Synthesis 1913
431 Meyer-Schuster Rearrangement 1917
432 Michael Addition 1922
433 Michaelis-Arbuzov Rearrangement 1929
434 Michael-Stetter Reaction 1935
435 Miescher Degradation 1940
436 Mignonac Reaction 1945
437 Milas Hydroxylation 1948
438 Mislow-Evans Rearrangement 1952
439 Mitsunobu Reaction 1955
440 MotTatt-Swern Oxidation 1962
441 Moore Cyclization 1967
442 Morgan-Walls Cyclization 1971
443 Mori-Ban Indole Synthesis 1975
444 Morin Rearrangement 1979
445 Moshers Acid 1983
446 Moureau-Mignonac Ketimine Synthesis 1988
447 Mukaiyama Aldol Reaction 1991
448 Mukaiyama-Michael Reaction 1996
449 Miiller-Cunradi-Piereh Process 2000
450 Myers-Saito Cyclization 2003
451 Nagata Reaction 2007
452 Nazarov Cyclization 2011
453 Neber Rearrangement 2017
454 Neber-Bossel Synthesis 2022
455 Nef Reaction 2025
456 Negishi Cross-Coupling 2029
457 Nencki Reaction 2035
458 Nenitzescu Synthesis 2038
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
XX CONTENTS
459 Nenitzescu Indole Synthesis 2042
460 Newman-Kwart Rearrangement 2046
461 Nicholas Reaction 2049
462 Niementowski Reaction 2054
463 Nierenstein Reaction 2058
464 Norrish Type I Reaction 2062
465 Norrish Type II Reaction 2067
466 Noyori Hydrogenation 2072
467 Nozaki-Hiyama-Kishi Reaction 2076
468 Nysted Reagent 2081
469 Ohle Quinoxaline Synthesis 2084
470 Oppenauer Oxidation 2088
471 Orton Rearrangement 2092
472 Ostromislensky Process 2097
473 Overman Rearrangement 2100
474 Paal-Knorr Furan Synthesis 2104
475 Paal-Knorr Pyrrole Synthesis 2107
476 Paneth Technique 2111
477 Parham Cyclization 2114
478 Parikh-Doering Oxidation 2118
479 Passerini Reaction 2121
480 Paterno-Buehl Reaction 2126
481 Pauson-Khand Reaction 2131
482 Payne Rearrangement 2139
483 Pearlmans Catalyst 2143
484 Pechmann Pyrazole Synthesis 2147
485 Pechmann Reaction 2151
486 Pellizzari Reaction 2157
487 Perkin Reaction 2160
488 Perkin Synthesis 2164
489 Perkow Reaction 2168
490 Petasis-Ferrier Rearrangement 2173
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
2042
2046
2049
2054
2058
2062
2067
2072
2076
2081
2084
2088
2092
2097
2100
2104
2107
2111
2114
2118
2121
2126
2131
2139
2143
2147
2151
2157
2160
2164
2168
2173
CONTENTS xxi
491 Peterson Olefination 2176
492 Petrenko-Kritschenko Piperidone Synthesis 2182
493 Pfau-Plattner Azulene Synthesis 2185
494 Pfitzinger Reaction 2188
495 Pfitzner-Moffatt Oxidation 2193
496 Phillips-Ladenburg Benzimidazole Synthesis 2197
497 Photo-Fries Rearrangement 2200
498 Pictet-Gams Synthesis 2206
499 Pictet-Spengler Reaction 2210
500 Piloty-Robinson Pyrrole Synthesis 2217
501 Pinacol Coupling Reaction 2221
502 Pinacol Rearrangement 2227
503 Pinner Condensation 2233
504 Pinner Reaction 2237
505 Pinner S-Triazine Synthesis 2241
506 Piria Reaction 2244
507 Plancher Rearrangement 2248
508 Polonovski Reaction 2251
509 Pomeranz-Fritsch Reaction 2256
510 Ponzio Reaction 2260
511 Prevost Reaction 2263
512 Prey Ether Cleavage 2267
513 Prilezhaev Reaction 2270
514 Prins Reaction 2275
515 Pudovik Reaction 2280
516 Pummerer Rearrangement 2284
517 Quelet Reaction 2290
PART THREE
518 Radziszewski Reaction 2293
519 Ramberg-Backlund Reaction 2298
520 Raney Nickel 2302
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xxii CONTENTS
521 Rauhut-Currier Reaction 2307
522 Reed Reaction 2311
523 Reformatsky Reaction 2314
524 Regitz Diazo Transfer 2322
525 ReilJy-Rickinbottom Rearrangement 2326
526 Reimer-Tiemann Reaction 2329
527 Reissert Compound 2335
528 Reissert Indole Synthesis 2341
529 Reppe Alkyne Cyclotrimerization 2345
530 Reppe Carbonylation 2352
531 Reppe Cyclization 2358
532 Reppe Vinylation 2362
533 Retro-Diels-Alder Reaction 2367
534 Retro-Ene Reaction 2373
535 Retropinacol Rearrangement 2378
536 Reverdin Rearrangement 2382
537 Riehm Quinoline Synthesis 2385
538 Rieke Metal 2388
539 Riemenschneider Reaction 2392
540 Riley Oxidation 2395
541 Ritter Reaction 2399
542 Robinson Annulation 2405
543 Robinson-Gabriel Oxazole Synthesis 2410
544 Robinson-Schopf Condensation 2414
545 Rosenmund Reaction 2418
546 Rosenmund Reduction 2421
547 Rosenmund-von Braun Reaction 2425
548 Rothemund Reaction 2429
549 Roush Crotylboration 2435
550 Rowe Rearrangement 2439
551 Rubottom Oxidation 2442
552 Ruff Degradation 2446
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
2307
2311
2314
2322
2326
2329
2335
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2341
2345
2352
I bullbullbullbullbullbullbullbullbullbullbullbullbullbull 2358
2362
2367
2373
2378
2382
2385
2388
2392
2395
2399
2405
2410
2414
2418
2421
2425
2429
2435
2439
2442
2446
CONTENTS xxiii
553 Rupe Rearrangement 2450
554 Sabatier-Senderens Reduction 2454
555 Saegusa Cyclization 2458
556 Saegusa Oxidation 2462
557 Sandmeyer Isatin Synthesis 2467
558 Sandmeyer Reaction 2471
559 Sarett Oxidation 2476
560 Saytzeff Rule 2480
561 Schiff Base 2484
562 Schlack-Kumpf Reaction 2488
563 Schlotterbeck Reaction 2491
564 Schmidlin Ketene Synthesis 2495
565 Schmidt Glycosylation 2498
566 Schmidt Reaction 2503
567 Schmidt-Rutz Reaction 2511
568 Schmittel Cyclization 2514
569 Scholl Reaction 2518
570 Schollkopf Bis-Lactim Ether Method 2523
571 Schollkopf Oxazole Synthesis 2529
572 Schonberg Rearrangement 2533
573 Schotten-Baumann Reaction 2536
574 Schwartz Reagent 2540
575 Screttas Lithiation 2544
576 Selenoxide Elimination 2548
577 Semmler-Wolff Aromatization 2552
578 Serini Reaction 2556
579 Seyferth-Gilbert Homologation 2559
580 Shapiro Reaction 2563
581 Sharpless Aminohydroxylation 2568
582 Sharpless Dihydroxylation 2574
583 Sharpless Epoxidation 2580
584 Shechter-Kaplan Oxidative Nitration 2586
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xxtv CONTENTS
585 Shi Epoxidation 2590
586 Simmons-Smith Reaction 2594
587 Simonini Reaction 2600
588 Skraup Reaction 2603
589 Smiles Rearrangement 2609
590 Sommelet Reaction 2615
591 Sommelet-Hauser Rearrangement bull 2620
592 Sonn-Miiller Reaction 2625
593 Sonogashira Coupling 2628
594 Staudinger [2+2] Cycloaddition 2636
595 Staudinger Reaction 2642
596 Stec Reaction 2647
597 Steglich Catalyst 2651
598 Steglich Rearrangement 2656
599 Stephen Reaction 2659
600 Stetter Reaction 2663
601 Stevens Rearrangement 2668
602 Stieglitz Rearrangement 2673
603 Stille Coupling 2677
604 Stohbe Condensation 2686
605 Stolle-Beeker Synthesis 2692
606 Stork Reaction 2695
607 Strecker Degradation 2701
608 Strecker Reaction 2707
609 Strecker Synthesis 2710
610 Suarez Cleavage 2718
611 Sugasawa Indole Synthesis 2722
612 Sugasawa Reaction 2726
613 Sundberg Indole Synthesis 2730
614 Suzuki Coupling 2733
615 Swarts Reaction 2744
616 Takai Olefination 2748
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
I bullbullbullbullbullbullbullbullbullbullbullbull
CONTENTS XXV
2590 617 Tebbe Olefination 2753
2744 647 von Braun Cyanogen Bromide Reaction 2896
2748 648 von Braun Degradation 2900
2594 618 ter Meer Reaction 2758
2600 619 Thiele-Winter Acetoxylation 2762
2603 620 Thorpe-Ziegler Cyclization 2766
2609 621 Tiemann Cyanohydrin Amination 2770
2615 622 Tiemann Rearrangement 2773
2620 623 Tlffeneau-Demjanov Ring Expansion 2777
2625 624 Tishchenko Reaction 2782
2628 625 Traube Purine Synthesis 2789
2636 626 Trofimov Reaction 2793
2642 627 Trost Desymmetrization 2797
2647 628 Truce-Smiles Rearrangement 2803
2651 629 Tscherniac-Einhorn Reaction 2807
2656 630 Tsuji-Trost Reaction 2812
2659 631 Twitchell Process 2817
2663 632 Tyrer Process 2822
2668 633 Ueno-Stork Cyclization 2826
2673 634 Ugi Reaction 2830
2677 635 Ullmann Acridine Synthesis 2838
2686 636 Ullmann Coupling 2842
2692 637 Ullmann Diaryl Ether Synthesis 2847
2695 638 Urech Cyanohydrin Method 2852
2701 639 Urech Hydantoin Synthesis 2856
2707 640 van Slyke Method 2860
2710 641 Varrentrapp Reaction 2864
2718 642 Victor Meyer Reaction 2868
2722 643 Vilsmeier Formylation 2872
2726 644 Vinylcyclopropane Rearrangement 2880
2730 645 Voigt Reaction 2888
2733 646 von Auwers Rearrangement 2892
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
xxvi CONTENTS
649 von Braun-Rudolf Synthesis 2904
650 von Richter Cinnoline Synthesis 2908
651 von Richter Reaction 2911
652 Vorbriiggen Glycosylation 2915
653 Wacker Oxidation 2920
654 Wagner-Jauregg Reaction 2926
655 Wagner-Meerwein Rearrangement 2930
656 Walden Inversion 2937
657 Wallach Rearrangement 2942
658 Weerman Reaction bull 2946
659 Weidenhagen Synthesis 2951
660 Weinreb Amide Formation 2956
661 Weinreb Ketone Synthesis 2963
662 Weiss-Cook Condensation 2968
663 Weitz-Scheffer Epoxidation 2975
664 Wender Indole Synthesis 2980
665 Wessely-Moser Rearrangement 2983
666 Westphalen Rearrangement 2988
667 Wharton Rearrangement 2994
668 Wibaut-Arens Alkylation 2998
669 Wichterle Reaction 3003
670 Widman-Stoermer Synthesis 3008
671 Wilkinsons Catalyst 3011
672 Willgerodt-Kindier Reaction 3018
673 Williamson Ether Synthesis bull 3026
674 Wittig Reaction 3031
675 [12]-Wittig Rearrangement 3043
676 [23]-Wittig Rearrangement 3049
677 Wohl Degradation 3056
678 WohlmiddotAue Reaction 3060
679 Wohler Synthesis bull 3064
680 Wohl-Ziegler Bromination 3067
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
2904
2908
2911
2915
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2920
2926
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull 2930
2937
2942
2946
2951
I bullbullbullbullbullbullbullbullbullbullbullbullbullbullbull
3067
2956
2963
2968
2975
2980
2983
2988
2994
2998
3003
3008
3011
3018
3026
3031
3043
3049
3056
3060
3064
CONTENTS xxvii
681 Wolff Rearrangement 3073
682 Wolffenstein-Boters Reaction 3081
683 Wolff-Kishner Reduction 3084
684 Woodward Cis-Hydroxylation 3090
685 Wurtz Synthesis 3094
686 Wurtz-Fittig Reaction 3100
687 Yamada Coupling 3105
688 Yamaguchi Esterification 3109
689 Zeisel Determination 3115
690 Zelinsky-Stadnikoff Reaction 3119
691 Zemplen Deacetylation 3123
692 Zerewitinoff Determination 3129
693 Ziegler Alcohol Synthesis 3134
694 Ziegler-Hafner Azulene Synthesis 3139
695 Zlegler-Natta Polymerization 3144
696 Zimmermann Reaction 3158
697 Zincke Disulfide Cleavage 3163
698 Zincke Nitration 3168
699 Zincke Reaction 3172
700 Zincke-Suhl Reaction 3178
701 Zinke Synthesis 3183
APPENDIXES
1 Schematic Reaction Index 3197
2 Reaction Type Summary 3323
3 Summary of Initial Publications on Named Organic Reactions 3341
4 Journal Abbreviation 3407
5 The Statistics of Reaction Published Years 3625
SUbject Index 3631
