Synthesis and crystal structure of a silyl-stabilized ally1 cation formed by disruption of an arene by a protonation-hydrosilylation sequence
- Author(s): Duttwyler, S
- Zhang, Y
- Linden, A
- Reed, CA
- Baldridge, KK
- Siegel, JS
- et al.
Published Web Locationhttps://doi.org/10.1002/anie.200900098
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.
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