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Synthesis and crystal structure of a silyl-stabilized allyl cation formed by disruption of an arene by a protonation-hydrosilylation sequence


Duttwyler, S; Zhang, Y; Linden, A; Reed, C A; Baldridge, K K; Siegel, J S (2009). Synthesis and crystal structure of a silyl-stabilized allyl cation formed by disruption of an arene by a protonation-hydrosilylation sequence. Angewandte Chemie International Edition, 48(21):3787-3790.

Abstract

Sly silyl caught in the act: Protonation of a mesitylene ring by the strongly acidic arenium carborane [CH(3)C(6)H(6)]- [CHB(11)Me(5)Br(6)] initiates a cascade reaction that results in a stable beta-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.

Sly silyl caught in the act: Protonation of a mesitylene ring by the strongly acidic arenium carborane [CH(3)C(6)H(6)]- [CHB(11)Me(5)Br(6)] initiates a cascade reaction that results in a stable beta-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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:17 April 2009
Deposited On:16 Jan 2010 19:45
Last Modified:05 Apr 2016 13:39
Publisher:Wiley-Blackwell
ISSN:1433-7851
Publisher DOI:10.1002/ange.200900098
PubMed ID:19378308

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