MECHANISM OF HETEROCYCLIC RING EXPANSIONS .3. REACTION OF PYRROLES WITH DICHLOROCARBENE

被引:31
作者
JONES, RL
REES, CW
机构
[1] King's College
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 17期
关键词
D O I
10.1039/j39690002249
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,5-Dimethyl-, 2,3,4,5-tetramethyl-, and 3,4-dimethyl-2,5-diphenyl-1H- pyrrole react with dichlorocarbene in basic solution to give 2-dichloromethyl-2H-pyrrole and 3-chloropyridines in low yield. However, in neutral aprotic solution high yields of 3-chloropyridines are formed in a synthetically useful reaction; 2H-pyrroles are not formed. These results support earlier mechanistic proposals.
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页码:2249 / &
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