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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
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 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.