Hydrosilylation of 3-substituted 1-propyne derivatives

Abstract

1. The reaction of triethylsilane with 3-substituted 1-propyne derivatives (HC≡CCH2X) leads to the formation of the addition products both by the Farmer rule (trans-isomer) and contrary to it (gem-isomer). Electronegative substituents cause the predominant formation of the gem-isomer. 2. The isomers of the hydrosilylation products can be identified on the basis of the IR spectral data from the bands of the stretching vibrations of the C=C bond for the trans-isomer, and from the frequencies of the stretching and deformation vibrations of the C-H bond of the =CH2 group for the gem-adduct.