Investigating the ring expansion reaction of pentaphenylborole and an azide

被引：80

作者：

Couchman, Shannon A. ^{[1
]}

Thompson, Trevor K. ^{[2
]}

Wilson, David J. D. ^{[1
]}

Dutton, Jason L. ^{[1
]}

Martin, Caleb D. ^{[2
]}

机构：

[1] La Trobe Univ, LaTrobe Inst Mol Sci, Dept Chem, Melbourne, Vic 3806, Australia

[2] Baylor Univ, Dept Chem & Biochem, Waco, TX 76798 USA

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 79期

基金：

澳大利亚研究理事会;

关键词：

RADICAL-ANION; FREE BOROLES; ANTIAROMATICITY; PENTAARYLBOROLES; ACTIVATION; REDUCTION; CHEMISTRY; SYSTEM;

D O I：

10.1039/c4cc04864d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction between trimethylsilyl azide and pentaphenylborole was recently shown to produce the corresponding 1,2-azaborine. Investigating this transformation theoretically suggests that the reaction proceeds via coordination of the azide to the borole, rearrangement to a bicyclic species, and conversion to a kinetically favoured eight-membered BN3C4 heterocycle or expulsion of N-2 to furnish the thermodynamically favoured 1,2-azaborine. The eight-membered species was structurally characterized as a borole adduct and represents an unusual analogue of cyclooctatetraene.

引用

页码：11724 / 11726

页数：3

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