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Open Access Publications from the University of California

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.

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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