Organosilicon compounds. Part XLVI. The reaction of bis(trimethylsilyl)mercury with ketones

Abstract

Bis(trimethylsilyl)mercury reacts with cyclohexanone at room temperature to give cyclohexyloxytrimethylsilane, cyclohexenyloxytrimethylsilane, and 1,1′-bis(trimethylsiloxy)bicyclohexyl. Acetone and acetophenone give analogous products. Bis(trimethylsilyl)mercury appears to react initially with one or two molar equivalents of the ketone R¹R²CO, to produce an intermediate radical R¹R²ĊO·SiMe₃, which dimerizes or disproportionates to give the observed products. Reactions of the mercurial with benzophenone, benzoquinone, mesityl oxide, and wet acetone have also been studied.