New insight into the mechanism of the reaction between α,β-unsaturated carbonyl compounds and triethylborane (Brown's reaction)

被引：35

作者：

Beraud, V

Gnanou, Y

Walton, JC

Maillard, B ^{[1
]}

机构：

[1] Univ Bordeaux 1, Chim Organ & Organomet Lab, CNRS, UMR 5802, F-33405 Talence, France

[2] Univ Bordeaux 1, Lab Chim Polymeres Organ, UMR 5629, ENSCPB,CNRS, F-33402 Talence, France

[3] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

boron and compounds; complexation; carbonyl compounds; enones; radicals and radical reactions;

D O I：

10.1016/S0040-4039(99)02279-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the reaction of alpha,beta-unsaturated carbonyl compounds with triethylborane under free radical conditions (Brown's reaction) including spectroscopic analyses (B-11 NMR, IR, EPR) of products and intermediates indicated that these reactions involve the prior formation of an 'alpha,beta-unsaturated carbonyl compound-organoborane' complex. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1195 / 1198

页数：4

共 16 条

[1] Regioselective alkylation of substituted quinones by trialkylboranes [J].