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The reactions of bridgehead adamantane derivatives with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine have been studied. The oxyfunctionalization process was found to proceed with excellent regioselectivity affording 3-substituted adamantan-1-ols in preparative chemical yields. The regioselectivity of the reaction was shown to tolerate various organic functional groups such as halogen, haloalkyl,...