Regio- and stereoselective rearrangements of formyl [2.2.1]bicyclic carbinols in methanol

Individual treatments of camphor- and camphene-derived formyl [2.2.1]bicyclic carbinols with blank methanol, methanol containing acidic acid, and methanol containing sodium methoxide provided corresponding [3.2.1]bicyclic hydroxy ketones. Rearrangement of each bicyclic carbinol was found to be regio- and stereoselective under neutral and acidic conditions. Mechanisms of these rearrangements were discussed.