REGIOSELECTIVE OXYFUNCTIONALIZATION OF BRIDGEHEAD ADAMANTANE DERIVATIVES

The reactions of bridgehead adamantane derivatives with perfluoro-cis- 2-n-butyl-3-n-propyloxaziridine have been studied. The oxyfunctionaliz ation process was found to proceed with excellent regioselectivity aff ording 3-substituted adamantan-1-ols in preparative chemical yields. T he regioselectivity of the reaction was shown to tolerate various orga nic functional groups such as halogen, haloalkyl, hydroxyl, carboxyl a nd carboalkoxyl. Mild reaction conditions, simplicity of the experimen tal procedure, high selectivity and chemical yields render this proces s an immediately useful and generalized approach to synthetically chal lenging polyfunctional adamantane derivatives. (C) 1997 Elsevier Scien ce Ltd.