Mechanism Studies of the Retropinacol Reaction

The purpose of this study was to synthesize the p-toluene-sulfates and methanesulfates of cis- and trans-2,2,5,5-tetramethyl-1,3-cyclohexanediol and to determine their behavior toward solvolytic and substitution reactions in regard to correlating possible rearrangements with a proposed mechanism for the retropinacol or Wagner-Meerwein rearrangements.