FREE-RADICAL CHEMISTRY OF IMINES

被引:46
|
作者
TOMASZEWSKI, MJ [1 ]
WARKENTIN, J [1 ]
WERSTIUK, NH [1 ]
机构
[1] MCMASTER UNIV,DEPT CHEM,HAMILTON,ON L8S 4M1,CANADA
关键词
D O I
10.1071/CH9950291
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group. When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated. However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines. Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered. Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.
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页码:291 / 321
页数:31
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