Additive in the carbodiimide method of peptide coupling, leading to decreased racemization: J. Am. Chem. Soc., 89, 7151 (1967). O-Alkylation followed by hydrazinolysis gives O-alkylhydroxylamines: Bull. Soc. Chim. Fr., 833 (1976). Copper-promoted coupling with arylboronic acids, followed by hydrazinolysis, affords O-arylhydroxylamines: Org. Lett., 3, 139 (2001). Efficient electron carrier for electrochemical oxidation of alcohols: J. Chem. Soc., Chem. Commun., 479 (1983). Has also been found to be an efficient catalyst for non-electrochemical oxidation of benzylic groups in benzonitrile solution with atmospheric pressure oxygen: J. Org. Chem., 60, 3934 (1995). The method can be extended to alkanes by the use of a catalyst such as 0.5-1 mol% Co(acac)2. Thus cyclohexane is oxidized to cyclohexanone and adipic acid; adamantane gives mainly 1-adamantanol with minor amounts of 2-adamantanone and 1,3-adamantanediol: J. Org. Chem., 61, 4520 (1996). Under similar conditions alkynes can be oxygenated to ɑ?-acetylenic ketones in good yields: Chem. Commun., 2037 (1998).
