Synthesis and crystal structure of a silyl-stabilized allyl cation formed by disruption of an arene by a protonation-hydrosilylation sequence.
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.
Duttwyler
Simon
S
Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
Zhang
Yun
Y
Linden
Anthony
A
Reed
Christopher A
CA
Baldridge
Kim K
KK
Siegel
Jay S
JS