The Complete Mechanism of an Aldol Condensation

被引：84

作者：

Perrin, Charles L. ^{[1
]}

Chang, Kuei-Lin ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 13期

基金：

美国国家科学基金会;

关键词：

AQUEOUS-SOLUTION; ELIMINATION REACTIONS; DEUTERIUM ISOTOPE; BETA-ELIMINATION; KINETICS; KETONES; WATER; INTERMEDIATE; ACETOPHENONE; ENOLIZATION;

D O I：

10.1021/acs.joc.6b00959

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although aldol condensation is one of the most important organic reactions, capable of forming new C-C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the C=C bond. This conclusion is based on a study of the partitioning ratios of the intermediate ketols and on the solvent kinetic isotope effects, whereby the condensations are faster in D2O than in H2O, regardless of substitution.

引用

页码：5631 / 5635

页数：5

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