Low-temperature reactions of dihalogenosilylenes, SiX2, with I2 or ICl in toluene yielding dihalogenoiodo(methylphenyl)silanes

Abstract

The gaseous silylenes, SiX₂(X = F, Cl, Br or I), have been condensed into solutions of I₂ or ICl in toluene at –90 °C to give a range of new compounds of formula SiX₂I(C₆H₄Me), demonstrating the generality of a type of reaction of silylenes first observed with SiO. All the products were mixtures of ortho, meta and para isomers but with an uncommonly high proportion of the ortho isomer in some cases. As the same iodosilane derivatives were obtained using I₂ or ICl as reagents, it is proposed that the reactions involve electrophilic attack of silylium ions, SiX₂I⁺, on the arene.