Oxidation of hydroxylamine derivatives. III. Anodic oxidation of N-hydoxy and N-alkoxycarbamates.

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Anodic oxidation of several N-hydroxycarbamates is studied by cyclic voltammetry and controlled potential electrolysis in acetonitrile with or without amines at a glassycarbon electrode. In the presence of excess amine, the corresponding N, O-dialkoxycarbonyl-and O-alkoxycarbonyl-N-hydroxycarbamates, alcohols and N-alkylacetamides, are produced from ethyl and benzyl N-hydroxycarbamates. N-Methylation of the compound markedly decreases the yields of the corresponding alcohol and N-alkylacetamide, whereas it increases O-alkoxycarbonylation of the starting compound and the demethylated product. O-Alkylated N-hydroxycarbamates yield N, N'-dialkoxycarbonyl-N, N'-dialkoxyhydrazines quantitatively. Plausible oxidation processes for these compounds are proposed.

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