q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF...

15
q7 'NT3 I öA÷ q&p ÜÙòÑñÖó ôÜÙòÑñÖó¿o> qp NTB¿Q ôKª·¶j¿¥©¶ ÔÖäðÑñt"»Ñ×ÜÑñt" ¥²*>¾¨Ìn¿w Ñ×ÜÑñ(axial posi-on) ÔÖäðÑñ(equatorial posi-on)

Transcript of q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF...

Page 1: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

q7"'NT�3�I�öA÷�

q&p�ÜÙòÑñÖó""ôÜÙòÑñÖó¿o �>"

"qp�NT�B¿Q� """""ôKª·¶j�¿�¥©¶""�

ÔÖäðÑñt"»Ñ×ÜÑñt"�

•  ¥²*�>¾¨­Ì�n�¿�w"•  Ñ×ÜÑñ�(axial"posi-on)"•  ÔÖäðÑñ�(equatorial"posi-on)�

Page 2: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

t"ÏL¬ux�

c���

•  7]ºÀÜÙòê×Ûóc¿o �>ª�«Ç²¥¿º c��ª�®ËDz¥"

•  Ñ×ÜÑñ�»ÔÖäðÑñ�Ài�-F²Ì¡�¥<|¿��¾¤Ì¡�

Page 3: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

c���

c��¾ÉË ÔÖäðÑñ�»Ñ×ÜÑñ�¿wF+ª"�G¾�ÍMÎÌ"

�wFÜÙòê×Ûó¿o �>�

•  úøü−ÝÑ×ÜÑñi��e(1,39diaxial"interac-on)�þ���!�

Page 4: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

®¿}À���

�wFÜÙòê×ÛóþÜÞ ¿,"�

wF+¾9²ÌÁ³Äi��eÏ"�²Ì�

ÜÞ À���¸ª#±ÔæñØõöR�ƨ½±Æ¿÷�

Page 5: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

�wFÜÙòê×ÛóþÜÞ ¿,"�

äïóÞ ºÀ�¸¿�>�¿ÔæñØõ:ª/«¥�

o �>¿56CÏ�r°¹ÄðȦ�

Page 6: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

.c?�2�

cis9ãÖðó»trans9ãÖðóÀi�-Fº«½¥�

âÞäÞâòóöÞâòÒå÷�

•  vcR�ÏE¸¡db[C/«¥"•  (6¯Í¶o �>ÏƸ�

Page 7: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

çÜÙòÑñÖó�

•  çÜÙò[2.2.1]êéßó"•  S��^s�

qýp�NT�B¿Q��

•  ���B"(addi-on"reac-on)""�¸¿�g`ª"ί·¹¼¿�2ÆdD`¾%ÃÍÌ"

•  y��Böelimina-on"reac-on)"Á»¸¿�g`ª�¸¿dD`¾�©ÍÌ"

"�

Page 8: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

•  wF�Bösubs-tu-on"reac-on)"�¸¿`�ª´ÍµÍ¿���ÏF°¹�¸¿I°¥dD`Ï�§Ì¡"

•  ���Börearrangement"reac-on)"Á»¸¿�g`ªt"»�2¿�RD¾ÉËI°¥fC Ïd±Ì,""

�BTR�

•  �BTR(reac-on"mechanism)"À��"

•  )�t"�~"(ëíðÜÞ,"homolysis)""t"ª9m¾�H¯ÍÌ," ïÝÖñ�B"

•  �)�t"�~"(êâòðÜÞ,"heterolysis)""t"ª�9m¾�H¯ÍÌ," PC�B"�

Page 9: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

ïÝÖñ�B�

•  ��2¾ÉÌt"@D �~"

•  �1→D�→�V"•  ���B�

PC�B�

•  PCt""��t"¿PCþ�Y�C=¿:�

Page 10: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

PC�B¿èÐÙßõ�

•  éòäó�Ϧ­Ì»/«¬[C�¯ÍÌ"

•  �2¿�Paö�Y�C=º½¥÷¿A�ª/«¥"l�ÇîÓsö�Pa�¥÷À�BC�¥"

ZO�{»Z�2�{�

•  ZO�{(nucleophile)""OöW¾;�÷Ï0Å¡�C©�¾;�°¹¥Ì¡"

•  Z�2�{(electrophile)"�2ö�¾;�÷Ï0Å¡�C©W¾;�°¹¥Ì¡"

"

Page 11: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

PC�B¿��

Ôâó¿HBÿ¿���B"�z¾ÀZ�2���B»°¹kÊ͹¥Ì¡"

ÑñÖó»ÑñÚó�

•  ÑñÚóÀ�2�8 ZOh�

Page 12: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

�BTRþ�BÀ�X��

→�ÖñìÖàÕó¿@D�

Kª·¶j�¿�e¢�B_£�

•  úù�2ZOn©ÊZ�2n¾$©·¹�¬"

•  ûùZO�{À�¾;�°¹¥Ì©�C"–  �¾;�°¹¥Ì�{À�2Ï\°¶Ê�C¾½Ì"

•  üùZ�2�{ÀW¾;�°¹¥Ì©�C"–  W¾;�°¹¥Ì�{À�2Ï ­�·¶Ê�C¾½Ì"

•  ý�ÕÙâáä�À4ÊÍÌ¡"

Page 13: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

Kª·¶j�¿L«J�

Page 14: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"
Page 15: q7'NT 3 I ö A÷labs.eng.hokudai.ac.jp/labo/organoelement/wp-content/...• wF Bösubs-tu-on"reac-on)" ¸¿` ª´ÍµÍ¿ Ï F ¹ ¸¿I ¥d D`Ï Ì¡" • Börearrangement"reac-on)"

ux�U¿�B¿Kª·¶j�ÏL¬¡�

C C

H

H H

H

H Br C C

H

H H

H

Br+

H HO

C C

H

H H

H

BrO

H

H– H+

C C

H

H H

H

BrO

H