We thank the Swiss and US National Science Foundation for research support.
Synthesis and Crystal Structure of a Silyl-Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation–Hydrosilylation Sequence†
Article first published online: 17 APR 2009
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 48, Issue 21, pages 3787–3790, May 11, 2009
How to Cite
Duttwyler, S., Zhang, Y., Linden, A., Reed, Christopher A., Baldridge, Kim K. and Siegel, Jay S. (2009), Synthesis and Crystal Structure of a Silyl-Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation–Hydrosilylation Sequence. Angew. Chem. Int. Ed., 48: 3787–3790. doi: 10.1002/anie.200900098
- Issue published online: 4 MAY 2009
- Article first published online: 17 APR 2009
- Manuscript Received: 7 JAN 2009
- US National Science Foundation
- allyl cations;
- silyl cations
Sly silyl caught in the act: Protonation of a mesitylene ring by the strongly acidic arenium carborane [CH3C6H6]- [CHB11Me5Br6] 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.