Stereochemistry of the oxymercuration of substituted methylenecyclohexanes and methylenecyclopentanes

Abstract

The oxymercuration–reduction of methylenecyclohexanes and methylenecyclopentanes in 50% aqueous tetrahydrofuran was studied. With unhindered methylenecyclohexanes attack of hydroxide ion occurs from the axial side of the molecule; the steric effect of the substituent is dominant in the reaction of hindered compounds. In the case of 2-substituted methylenecyclopentanes, the hydroxide ion attacks from the same side as the substituent. The stereochemistry of this reaction is discussed.