Abstract
Anodic oxidation of N-alkylhydroxylamines with and without a β-hydroxy group was studied by cyclic voltammetry and controlled potential electrolysis in aqueous buffer solution of pH 8.8. The hydroxylamines with a β-hydroxy group were oxidized initially to the corresponding nitroxides and gave the final products via two routes ; i) cleavage of the (α) C-(β) C bond to give aldehydes and oximes, and ii) disproportionation of the nitroxides to form the nitroso compounds. The hydroxylamines without a β-hydroxy group did not undergo cleavage of the (α) C-(β) C bond and gave nitroso compounds. Substituents on the α and β carbons affected the product distribution. When a phenyl group or two methyl groups were present on the (β) C, or one methyl group was present on both (α) C and (β) C, (α) C-(β) C bond cleavage was predominant.
