CARBENOID VERSUS VINYLOGOUS REACTIVITY IN RHODIUM(II)-STABILIZED VINYLCARBENOIDS

被引：80

作者：

DAVIES, HML

HU, BH

SAIKALI, E

BRUZINSKI, PR

机构：

[1] Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II)-stabilized vinylcarbenoid intermediates display electrophilic character at both the carbenoid site and the vinylogous position. The solvent and catalyst as well as the vinylcarbenoid structure have major effects on the regiochemical outcome of the reaction of vinylcarbenoids with alkenes and dienes. Reaction of vinylcarbenoids with vinyl ethers can lead to the formation of either cyclopropanes or cyclopentenes while reaction of vinylcarbenoids with cyclopentadiene can lead to the formation of either bicyclo[3.2.1]octadiene or bicyclo[2.2.1]heptene derivatives.

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页码：4535 / 4541

页数：7

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