HYDROGEN ABSTRACTION REACTIONS OF DIPHENYLPICRYLHYDRAZYL

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Abstract
The stable free radical diphenylpicrylhydrazyl (DPP•) has been found to react quantitatively with ammonia and hydrazine forming nitrogen and diphenylpicrylhydrazine, and less cleanly with hydroxylamine forming diphenylpicrylhydrazine and nitrous oxide. The reactions of DPP• with a variety of amines are not clean, in part owing to the formation of complexes of the amines with the reaction product diphenylpicrylhydrazine. Preliminary investigations of the reactions of DPP• with mercaptans have shown that these otherwise clean reactions have a variable stoichiometry, dependent on the concentration and other reaction conditions.