Halomethyl-metal compounds : XXXV. The preparation of dibromomethyl and bromochloromethyl derivatives of silicon and germanium by the (trihalomethyl)mercurial route and their reduction to monohalomethyl compounds

Abstract

The reaction of phenyl(dibromochloromethyl)mercury and phenyl(tribromomethyl)mercury with organosilicon and organogermanium hydrides gave bromochloromethyl- and dibromomethyl-substituted derivatives of silicon and germanium via dihalocarbene insertion into the SiH and GeH bonds. The reduction of these products with tri-n-butyltin hydride at room temperature gave the respective monohalomethyl compounds, the bromochloromethyl derivatives being reduced to the chloromethyl compounds, the dibromomethyl derivatives to the bromomethyl compounds. Excellent yields were obtained in both steps of this new synthesis of monohalomethyl derivatives of silicon and germanium.