Functional group selectivity in reactions of epoxides with tungsten hexachloride

The reactivity of several cyclohexene oxides bearing various functional groups toward the reagent tungsten hexachloride is reported. In general, the conversion of the epoxide to the trans dichloride occurs relatively rapidly. Several groups proved stable—esters, sulfides, sulfones, hindered silyl ethers—while others were unstable—alcohols, unhindered silyl ethers, ketones. The diaxial dichloride is usually formed although the diequatorial dichloride could also be prepared.