Mechanistic Aspects of Alkyne Migration in Alkylidene Carbenoid Rearrangements

被引：28

作者：

Bichler, Paul ^{[1
]}

Chalifoux, Wesley A. ^{[1
]}

Eisler, Sara ^{[1
]}

Shun, Annabelle L. K. Shi ^{[1
]}

Chernick, Erin T. ^{[1
]}

Tykwinski, Rik R. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 03期

基金：

加拿大自然科学与工程研究理事会;

关键词：

BUTTENBERG-WIECHELL REARRANGEMENT; ACETYLENE REARRANGEMENT; UNSATURATED CARBENES; ORGANIC-SYNTHESIS; POLYYNE SYNTHESIS; STEREOCHEMISTRY; CYCLOADDITIONS; 1,3-BUTADIYNES; CYCLOPROPENE; APTITUDES;

D O I：

10.1021/ol8023665

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the Fritsch-Buttenberg-Wiechell rearrangement of C-13 labeled precursors has been examined to determine the propensity of the alkynyl (R-C C-) group to migrate in an alkylidene carbenoid species. Reaction of dibromoolefins with n-BuLi and ketones with Me3SiC(Li)N-2 both demonstrate that the alkynyl moiety readily undergoes 1,2-migration from carbenoid intermediates.

引用

页码：519 / 522

页数：4

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