Carbenoids by deoxygenation of carbonyl compounds with chloromethylsilanes

Abstract

Deoxygenation of benzophenone, benzaldehyde, and cyclohexanone with chloromethylsilanes and zinc–copper couple in ether is reported to yield 2,2,2-triphenylacetophenone, a mixture of deoxybenzoin and diphenyl-acetaldehyde, and a bicyclic ketone with the proposed 2-oxocycloheptanespirocyclohexane structure, respectively; a carbene mechanism is proposed.