Oxidation of Alcohols with Nitroxyl Radical Resins under Two-Phase Conditions

The oxidation of alcohols to carbonyl compounds such as aldehydes and ketones was studied using potassium hexacyano­ferrate (III) mediated by nitroxyl radical polystyrene resins as catalyst under organic-aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no overoxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. Oxidative cyclization of 1,4- and 1,5-diols to (gamma)- and (delta)-lactones, respectively, proceeded nicely.