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

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

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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

Author(s) -

Duttwyler Simon,

Zhang Yun,

Linden Anthony,

Reed Christopher A.,

Baldridge Kim K.,

Siegel Jay S.

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200900098

Subject(s) - silylation , protonation , chemistry , mesitylene , hydrosilylation , cationic polymerization , ring (chemistry) , medicinal chemistry , crystal structure , carborane , stereochemistry , photochemistry , polymer chemistry , organic chemistry , catalysis , ion

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 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.

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