Rearrangements of trihalomethyl ketones

被引：11

作者：

Braverman, S ^{[1
]}

Cherkinsky, M ^{[1
]}

Kumar, EVKS ^{[1
]}

Gottlieb, HE ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON | 2000年 / 56卷 / 26期

基金：

美国国家科学基金会;

关键词：

ketone; Favorskii rearrangement; gamma-elimination;

D O I：

10.1016/S0040-4020(00)00360-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trihalomethyl ketones have been prepared and their reactivity under basic conditions was investigated in terms of competition between 1,2- vs. 1,3-elimination and nucleophilic substitution. Favorskii rearrangement was the preferred process, but in those cases where electronic or steric effects were present, nucleophilic substitution became dominant. No evidence of ketene formation was detected. The mechanism of formation of the various rearrangement products is discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4521 / 4529

页数：9