Ion-Cyclotron Resonance Studies of Alkylsilyl Ions. I. The Reactions Between Alcohols and the Trimethylsilyl Cation

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Abstract
Nucleophilic attack of an alcohol (ROH) at the electrophilic silicon centre of the trimethylsilyl cation (Me3Si+) produces the 1 : 1 adduct Me3-O+(H)R(1). The adduct may fragment by loss of methane to yield Me2Si+-O-R; and this elimination is most pronounced when R = Me. When R ≥ C2H5, the major decomposition pathway of (1) involves elimination of the alkene [R-H] to produce Me3Si-O+H2, which may undergo further reaction with the neutral alcohol to reform (1). The proton transfer which accompanies the elimination of [R- H] from (1) originates predominantly from C2 of the alcohol; this suggests the intermediacy of a four-membered transition state in this reaction.

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