On the mechanism of the intramolecular samarium Barbier reaction. Probes for formation of radical and organosamarium intermediates

被引:67
作者
Curran, DP
Gu, X
Zhang, W
Dowd, P
机构
[1] Department of Chemistry, University of Pittsburgh, Pittsburgh
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4020(97)00608-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new type of mechanistic probe for the intramolecular samarium Barbier reaction has been designed, and two different probe substrates have been investigated in detail. Remarkably, no unambiguous evidence could be obtained in favor of any of the obvious intermediates (free alkyl or alkoxy radicals, ketyls, organosamarium species) that are postulated for this reaction. Several possibilities for modified mechanisms are suggested. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:9023 / 9042
页数:20
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