REGIOSELECTIVITY IN GAS-PHASE ELIMINATION-REACTIONS - 1,2 VS 1,4 AND ALLENIC ION VS DIENIDE FORMATION

被引：9
|
作者：
RABASCO, JJ [1 ]
KASS, SR [1 ]
机构：
[1] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 05期
关键词：
GAS-PHASE; ELIMINATIONS; REGIOCHEMISTRY; FLOWING AFTERGLOW; METHYL ETHERS;
D O I：
10.1016/0040-4039(93)89006-C
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Gas-phase elimination reactions of deuterium labeled 1-allyl-1-methoxy-6,6-dimethyl-2-cyclohexene (1), 1-methoxy-4,4-dimethyl-1-vinyl-2-cyclohexene (2) and 3-methoxy-3-methyl-1-butene (3) have been investigated. 1,2-Elimination is the favored pathway when 1 reacts with hydroxide (3.5:1) and methoxide (2.6:1), but 1,4-elimination is preferred with fluoride by 2:1. Abstraction of a vinyl proton is the elimination reactions of 2 and 3 is dominant when amide and/or dimethylamide are used, whereas the loss of an alkyl proton is heavily favored with hydroxide.
引用
收藏
页码：765 / 768
页数：4
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