Oxidation of N-Alkylhydroxylamines. I. Nitroxides formed on Oxidation of N-Alkylhydroxylamines with Lead Tetraacetate

Abstract

N-Alkylhydroxylamines are shown to be easily oxidized to corresponding nitroso compounds with lead tetraacetate in benzene. The N-alkylhydroxylamines are found to react with equimolar lead tetraacetate and corresponding alkylnitroxides are detected during the oxidation. These results propose a mechanism in which lead tetraacetate acts as a hydrogen abstracting oxidant and the N-alkylhydroxylamines are oxidized to nitroso compounds via corresponding alkylnitroxides.