
%0 Journal Article
%A Blair, IA 
%A Phillipou, G 
%A Bowie, JH 
%T Ion-Cyclotron Resonance Studies of Alkylsilyl Ions. I. The Reactions Between Alcohols and the Trimethylsilyl Cation
%J Australian Journal of Chemistry
%D 1979/01/01
%V 32
%N 1
%P 59-64
%K 
%R https://doi.org/10.1071/CH9790059
%U https://www.publish.csiro.au/paper/CH9790059 
%X 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 &#8805; 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. 
