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Article
Peer Reviewed

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

Duttwyler, Simon;
Zhang, Yun;
Linden, Anthony;
Reed, Christopher A;
Baldridge, Kim K;
Siegel, Jay S

UC Riverside Previously Published Works (2009)

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.

Cover page: Synthesis and Crystal Structure of a Silyl‐Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation–Hydrosilylation Sequence