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.
Organic Chemistry Institute, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.
Simon
S
Duttwyler
Yun
Y
Zhang
Anthony
A
Linden
Christopher A
CA
Reed
Kim K
KK
Baldridge
Jay S
JS
Siegel