MECHANISM OF ALPHA-SUBSTITUTION REACTIONS OF ACRYLIC DERIVATIVES

被引：118

作者：

HILL, JS ^{[1
]}

ISAACS, NS ^{[1
]}

机构：

[1] UNIV READING,DEPT CHEM,POB 224,READING RG6 2AD,BERKS,ENGLAND

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1990年 / 3卷 / 05期

关键词：

D O I：

10.1002/poc.610030503

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions between acrylic esters, nitriles and similar compounds on the one hand and aldehydes and ketones on the other, catalysed by tertiary amines, lead to α‐(hydroxyalkyl)acrylic compounds. Evidence on the basis of kinetics, volumes of activation and of reaction, and kinetic isotope effects is presented to deduce a mechanism in which amine first undergoes Michael addition, the resulting enolate ion adds to the carbonyl compound in a rate‐determining step and finally base is eliminated. An analysis of the solvent effect on rates is also presented. Copyright © 1990 John Wiley & Sons Ltd.

引用

页码：285 / 288

页数：4

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