Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated...
Transcript of Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated...
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Supporting Information
Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates
John Kallikat Augustine,* a Agnes Bombrun,b Srinivasa Venkatachaliah,a Anandh Jothia
aSyngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link
Road, Bangalore - 560 099, India.
bCovance Central Laboratory Services, 7 Rue Moise-Marcinhes, 1217 Meyrin, Geneva, Switzerland.
Table of contents
Table of contents.………………………………………………….... 1 1H NMR, 13C NMR, HPLC and IR reports for 1aE…….………… 2-5 1H NMR, 13C NMR, HPLC and IR reports for 1a-1q…….………… 6-73 1H NMR, 13C NMR, HPLC and IR reports for 2a-2j……….………. 74-113 1H NMR, 13C NMR, HPLC and IR reports for 3a-3i……….………. 114-149 1H NMR, 13C NMR, HPLC and IR reports for 4a-4j……….………. 150-189 1H NMR, 13C NMR reports for 5 …………………….……….……. 190-191
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(E)-isomer (1aE): 1H NMR (400 MHz) in DMSO-d6
Br
BrCOOMe
H
1aE
delta 7.54 ppm
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13C NMR (100 MHz) in CDCl3 (1aE)
Br
BrCOOMe
1aE
(E)
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IR data (1aE)
Br
BrCOOMe
1aE
(E)
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HPLC data (1aE)
Br
BrCOOMe
1aE
(E)
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(Z)-isomer (1a): 1H NMR (400 MHz) in DMSO-d6
Br
COOMe
Br
H
1a
delta 8.25 ppm
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13C NMR (100 MHz) in CDCl3 (1a)
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IR spectrum (1a)
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HPLC data (1a)
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1H NMR (400 MHz) in CDCl3 (1b)
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13C NMR (100 MHz) in CDCl3 (1b)
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IR spectrum (1b)
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HPLC data (1b)
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1H NMR (400 MHz) in CDCl3 (1c)
Br
O
O(Z)
(1c)N
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13C NMR (100 MHz) in CDCl3 (1c)
Br
O
O(Z)
(1c)N
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IR spectrum (1c)
Br
O
O(Z)
(1c)N
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HPLC data (1c)
Br
O
O(Z)
(1c)N
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1H NMR (400 MHz) in DMSO-d6 (1d)
Br
O
O
O
O
(Z)
(1d)
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13C NMR (100 MHz) in CDCl3 (1d)
Br
O
O
O
O
(Z)
(1d)
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IR spectrum (1d)
Br
O
O
O
O
(Z)
(1d)
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HPLC data (1d)
Br
O
O
O
O
(Z)
(1d)
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1H NMR (400 MHz) in CDCl3 (1e)
Br
O
O
Br
Cl(Z)
(1e)
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13C NMR (100 MHz) in CDCl3 (1e)
Br
O
O
Br
Cl(Z)
(1e)
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24
IR spectrum (1e)
Br
O
O
Br
Cl(Z)
(1e)
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HPLC data (1e)
Br
O
O
Br
Cl(Z)
(1e)
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1H NMR (400 MHz) in CDCl3 (1f)
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27
13C NMR (100 MHz) in CDCl3 (1f)
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IR spectrum (1f)
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29
HPLC data (1f)
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1H NMR (400 MHz) in CDCl3 (1g)
O
O
BrNC
(Z)
(1g)
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13C NMR (100 MHz) in CDCl3 (1g)
O
O
BrNC
(Z)
(1g)
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32
IR spectrum (1g)
O
O
BrNC
(Z)
(1g)
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33
HPLC data (1g)
O
O
BrNC
(Z)
(1g)
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34
1H NMR (400 MHz) in CDCl3 (1h)
O
O
Br
(Z)
(1h)
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35
13C NMR (100 MHz) in CDCl3 (1h)
O
O
Br
(Z)
(1h)
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36
IR spectrum (1h)
O
O
Br
(Z)
(1h)
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HPLC data (1h)
O
O
Br
(Z)
(1h)
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38
1H NMR (400 MHz) in DMSO-d6 (1i)
( Z )
(1i)N
Br
COOMe
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39
13C NMR (100 MHz) in DMSO-d6 (1i)
( Z )
(1i)N
Br
COOMe
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40
IR spectrum (1i)
( Z )
(1i)N
Br
COOMe
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41
HPLC data (1i)
( Z )
(1i)N
Br
COOMe
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42
1H NMR (400 MHz) in CDCl3 (1j)
NBr
O
O
F
F
( Z)
(1j)
F
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43
13C NMR (100 MHz) in CDCl3 (1j)
NBr
O
O
F
F
( Z)
(1j)
F
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44
IR spectrum (1j)
NBr
O
O
F
F
( Z)
(1j)
F
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45
HPLC data (1j)
NBr
O
O
F
F
( Z)
(1j)
F
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46
1H NMR (400 MHz) in CDCl3 (1k)
(1k)Br
COOMeSBr
(Z)
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47
13C NMR (100 MHz) in CDCl3 (1k)
(1k)Br
COOMeSBr
(Z)
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48
IR spectrum (1k)
(1k)Br
COOMeSBr
(Z)
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49
HPLC data (1k)
(1k)Br
COOMeSBr
(Z)
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50
1H NMR (400 MHz) in CDCl3 (1l)
(Z)
(1l)Br
COOMeO
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51
13C NMR (100 MHz) in CDCl3 (1l)
(Z)
(1l)Br
COOMeO
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52
IR spectrum (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 53: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/53.jpg)
53
HPLC data (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 54: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/54.jpg)
54
1H NMR (400 MHz) in CDCl3 (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 55: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/55.jpg)
55
13C NMR (100 MHz) in CDCl3 (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 56: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/56.jpg)
56
IR spectrum (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 57: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/57.jpg)
57
HPLC data (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 58: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/58.jpg)
58
1H NMR (400 MHz) in CDCl3 (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 59: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/59.jpg)
59
13C NMR (100 MHz) in CDCl3 (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 60: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/60.jpg)
60
IR spectrum (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 61: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/61.jpg)
61
HPLC data (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 62: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/62.jpg)
62
1H NMR (400 MHz) in CDCl3 (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 63: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/63.jpg)
63
13C NMR (100 MHz) in CDCl3 (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 64: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/64.jpg)
64
IR spectrum (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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65
HPLC data (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 66: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/66.jpg)
66
1H NMR (400 MHz) in CDCl3 (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 67: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/67.jpg)
67
13C NMR (100 MHz) in CDCl3 (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 68: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/68.jpg)
68
IR spectrum (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 69: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/69.jpg)
69
HPLC data (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 70: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/70.jpg)
70
1H NMR (400 MHz) in DMSO-d6 (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 71: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/71.jpg)
71
13C NMR (100 MHz) in DMSO-d6 (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 72: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/72.jpg)
72
IR spectrum (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 73: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/73.jpg)
73
HPLC data (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 74: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/74.jpg)
74
1H NMR (400 MHz) in DMSO-d6 (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 75: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/75.jpg)
75
13C NMR (100 MHz) in DMSO-d6 (2a)
ClO
O(Z)
(2a)
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![Page 76: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/76.jpg)
76
IR spectrum (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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77
HPLC data (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 78: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/78.jpg)
78
1H NMR (400 MHz) in DMSO-d6 (2b)
ClO
O(Z)
Br(2b)
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79
13C NMR (100 MHz) in DMSO-d6 (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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80
IR spectrum (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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81
HPLC data (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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82
1H NMR (400 MHz) in DMSO-d6 (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 83: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/83.jpg)
83
13C NMR (100 MHz) in DMSO-d6 (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 84: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/84.jpg)
84
IR spectrum (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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85
HPLC data (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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86
1H NMR (400 MHz) in CDCl3 (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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87
1H NMR (100 MHz) in CDCl3 (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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88
IR spectrum (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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89
HPLC data (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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90
1H NMR (400 MHz) in CDCl3 (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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91
13C NMR (100 MHz) in CDCl3 (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 92: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/92.jpg)
92
IR spectrum (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 93: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/93.jpg)
93
HPLC data (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 94: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/94.jpg)
94
1H NMR (400 MHz) in DMSO-d6 (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 95: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/95.jpg)
95
13C NMR (100 MHz) in DMSO-d6 (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 96: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/96.jpg)
96
IR spectrum (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 97: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/97.jpg)
97
HPLC data (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 98: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/98.jpg)
98
1H NMR (400 MHz) in DMSO-d6 (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 99: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/99.jpg)
99
13C NMR (100 MHz) in DMSO-d6 (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 100: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/100.jpg)
100
IR spectrum (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 101: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/101.jpg)
101
HPLC data (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 102: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/102.jpg)
102
1H NMR (400 MHz) in CDCl3 (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 103: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/103.jpg)
103
13C NMR (100 MHz) in CDCl3 (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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104
IR spectrum (2h)
O
O
ClO2N
(Z)
(2h)
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105
HPLC data (2h)
O
O
ClO2N
(Z)
(2h)
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106
1H NMR (400 MHz) in CDCl3 (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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107
13C NMR (100 MHz) in CDCl3 (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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108
IR spectrum (2i)
O
O
Cl
(Z)
(2i)
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109
HPLC data (2i)
O
O
Cl
(Z)
(2i)
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110
1H NMR (400 MHz) in CDCl3 (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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111
13C NMR (100 MHz) in CDCl3 (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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112
IR spectrum (2j)
O
O
Cl
(Z)
(2j)
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113
HPLC data (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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114
1H NMR (400 MHz) in CDCl3 (3a)
F
O
O(Z)
(3a)
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115
13C NMR (100 MHz) in CDCl3 (3a)
F
O
O(Z)
(3a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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116
IR spectrum (3a)
F
O
O(Z)
(3a)
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117
HPLC data (3a)
F
O
O(Z)
(3a)
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118
1H NMR (400 MHz) in CDCl3 (3b)
BrF
O
O(Z)
(3b)
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119
13C NMR (100 MHz) in CDCl3 (3b)
BrF
O
O(Z)
(3b)
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120
IR spectrum (3b)
BrF
O
O(Z)
(3b)
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121
HPLC data (3b)
BrF
O
O(Z)
(3b)
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122
1H NMR (100 MHz) in CDCl3 (3c)
OF
O
O(Z)
(3c)
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123
13C NMR (100 MHz) in CDCl3 (3c)
OF
O
O(Z)
(3c)
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124
IR spectrum (3c)
OF
O
O(Z)
(3c)
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125
HPLC data (3c)
OF
O
O(Z)
(3c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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126
1H NMR (400 MHz) in CDCl3 (3d)
NCF
O
O(Z)
(3d)
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127
13C NMR (100 MHz) in CDCl3 (3d)
NCF
O
O(Z)
(3d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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128
IR spectrum (3d)
NCF
O
O(Z)
(3d)
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129
HPLC data (3d)
NCF
O
O(Z)
(3d)
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130
1H NMR (400 MHz) in CDCl3 (3e)
NO2
F
F
FF
O
O(Z)
(3e)
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131
13C NMR (100 MHz) in CDCl3 (3e)
NO2
F
F
FF
O
O(Z)
(3e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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132
IR spectrum (3e)
NO2
F
F
FF
O
O(Z)
(3e)
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133
HPLC data (3e)
NO2
F
F
FF
O
O(Z)
(3e)
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134
1H NMR (400 MHz) in CDCl3 (3f)
O
F
O
O
(Z)
(3f )
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135
13C NMR (100 MHz) in CDCl3 (3f)
O
F
O
O
(Z)
(3f )
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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136
IR spectrum (3f)
O
F
O
O
(Z)
(3f )
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137
HPLC spectrum (3f)
O
F
O
O
(Z)
(3f )
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138
1H NMR (400 MHz) in CDCl3 (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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139
13C NMR (100 MHz) in CDCl3 (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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140
IR spectrum (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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141
HPLC data (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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142
1H NMR (400 MHz) in CDCl3 (3h)
FO
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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143
13C NMR (100 MHz) in CDCl3 (3h)
F
O
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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144
IR spectrum (3h)
FO
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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145
HPLC data (3h)
F
O
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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146
1H NMR (400 MHz) in CDCl3 (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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147
13C NMR (100 MHz) in CDCl3 (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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148
IR spectrum (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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149
HPLC data (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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150
1H NMR (400 MHz) in CDCl3 (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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151
13c NMR (100 MHz) in CDCl3 (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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152
IR spectrum (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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153
HPLC spectrum (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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154
1H NMR (400 MHz) in CDCl3 (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
![Page 155: Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general](https://reader030.fdocuments.net/reader030/viewer/2022040304/5e9b1c3d65beee5fd212a254/html5/thumbnails/155.jpg)
155
13c NMR (100 MHz) in CDCl3 (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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156
IR spectrum (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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157
HPLC data (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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158
1H NMR (400 MHz) in CDCl3 (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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159
13C NMR (100 MHz) in CDCl3 (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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160
IR spectrum (4c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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161
HPLC data (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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162
1H NMR (400 MHz) in CDCl3 (4d)
IO
O(Z)
CN 4d
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163
13C NMR (100 MHz) in CDCl3 (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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164
IR spectrum (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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165
HPLC data (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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166
1H NMR (400 MHz) in CDCl3 (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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167
13C NMR (100 MHz) in CDCl3 (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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168
IR spectrum (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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169
HPLC data (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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170
1H NMR (400 MHz) in CDCl3 (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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171
13C NMR (100 MHz) in CDCl3 (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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172
IR spectrum (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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173
HPLC data (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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174
1H NMR (400 MHz) in CDCl3 (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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175
13C NMR (100 MHz) in CDCl3 (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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176
IR spectrum (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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177
HPLC data (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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178
1H NMR (400 MHz) in DMSO-d6 (4h)
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179
13C NMR (100 MHz) in DMSO-d6 (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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180
IR spectrum (4h)
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181
HPLC data (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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182
1H NMR (400 MHz) in CDCl3 (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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183
13C NMR (100 MHz) in CDCl3 (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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184
IR spectrum (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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185
HPLC data (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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186
1H NMR (400 MHz) in CDCl3 (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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187
13C NMR (100 MHz) in CDCl3 (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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188
IR spectrum (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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189
HPLC data (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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190
1H NMR (400 MHz) in CDCl3 (5)
O
OO
O
(5)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
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191
13C NMR (100 MHz) in CDCl3 (5)
**************************
O
OO
O
(5)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013