Tetrabromobutatriene: Completing the perhalocumulene series

被引：36

作者：

Liu, PH ^{[1
]}

Li, L ^{[1
]}

Webb, JA ^{[1
]}

Zhang, Y ^{[1
]}

Goroff, NS ^{[1
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 13期

关键词：

D O I：

10.1021/ol049734x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br-2 at -25 degreesC in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.

引用

页码：2081 / 2083

页数：3

共 21 条

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