Halomethyl-metal compounds XXVII. The Reaction of Phenyl(Dihalomethyl)Mercury Compounds with Organosilicon Hydrides: A Preparation of Halomethyl-Silicon Compounds

Abstract

Phenyl(dihalomethyl)mercury compounds, PhHgCBr 2H and PhHgCClBrH, have been found to transfer CHBr and CHCl, respectively, to organosilicon hydrides forming (bromomethyl)- and (chloromethyl)silanes. Such reactions appear to be of preparative utility only in the case of alkylsilicon hydrides. (Bromomethyl)triethylgermane also was prepared in moderate yield by this procedure. (Dibromomethyl)mercuric bromide by itself was not a CHBr transfer agent, but did become effective in this application when an equivalent of diphenylmercury was added to it. It was found that diphenylmercury “activates” (dibromomethyl)mercuric bromide by reacting with it to form phenylmercuric bromide and phenyl(dibromomethyl)mercury.