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Abstract
Aerobic oxidation of various sulfides using N-hydroxyphthalimide (NHPI) in the presence of alcohols was examined. For instance, the oxidation of diphenyl sulfide in the presence of cyclohexanol and a catalytic amount of NHPI in benzonitrile gave diphenyl sulfoxide in 88 % yield along with a small amount of diphenyl sulfone (7 %). The actual oxidant in this oxidation is considered to be an α-hydroxy hydroperoxide generated by the autoxidation of alcohol assisted by the NHPI which serves as the radical catalyst.
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