Organoboranes in organic synthesis. II. The mechanism of the reaction of α,α'-dibromo ketones with organoboranes in the presence of base

Abstract

The mechanism of the reaction of α,α-dibromocyclohexanones with organoboranes has been investigated, and is suggested to occur by attack of base on bromine in the ketone-borane adduct, followed by rate-determining alkyl group transfer from boron to carbon. Labelling studies show that the extra proton in the products comes from the solvent, tetrahydrofuran.