Silylcarbonium ions from the reaction of silylcarbinols with boron trifluoride

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Abstract
The behavior of silylcarbonium ions, Si—C+, generated from various types of α-silylcarbinol with boron trifluoride under a variety of conditions of temperature and solvent has been examined. Four distinct types of reaction have been observed, depending on the conditions and the structure of the carbinol. These are: 1,2-migration of aryl groups from silicon to carbon, yielding a fluorosilane; Friedel–Crafts substitution of the carbonium ion on an aromatic substrate; elimination of the elements of water to give a vinylsilane; and isomerization to the β-silylcarbonium ion by hydrogen migration, followed by elimination of the silyl group to give a simple fluorosilane and an alkene (i.e. a β-elimination). Factors affecting the partitioning between these pathways are discussed.

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