Synthesis and Crystal Structure of a Silyl-Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation-Hydrosilylation Sequence

被引：23

作者：

Duttwyler, Simon ^{[2
]}

Zhang, Yun ^{[1
]}

Linden, Anthony ^{[2
]}

Reed, Christopher A. ^{[1
]}

Baldridge, Kim K. ^{[2
]}

Siegel, Jay S. ^{[2
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Ctr S&P Block Chem, Riverside, CA 92521 USA

[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 21期

基金：

美国国家科学基金会;

关键词：

allyl cations; arenes; carboranes; hyperconjugation; silyl cations; X-RAY-STRUCTURE; STABLE PENTAMETHYLCYCLOPENTADIENYL CATION; INORGANIC-CHEMISTRY; MOLECULAR-STRUCTURE; VINYL CATION; BETA; CARBOCATIONS; CONJUGATION; ELEMENTS; SILICON;

D O I：

10.1002/anie.200900098

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sly silyl caught in the act: Protonation of a mesitylene ring by the strongly acidic arenium carborane [CH3C6H6]- [CHB11Me5Br6] initiates a cascade reaction that results in a stable β-silyl allyl cation (see picture, H yellow, C blue, silyl allyl group red). Remarkably, the driving force in the reaction suffices to disrupt a stable aromatic ring in favor of a cationic reactive intermediate. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3787 / 3790

页数：4

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