920-40-1Relevant academic research and scientific papers
Oxidation of Hydroxylamine Derivatives. VI. Anodic Oxidation of N-Alkyl-β-hydroxyhydroxylamines in Aqueous Buffer Solution
Ozaki, Shigeko,Nishiguchi, Susumu,Masui, Masaichiro
, p. 2609 - 2616 (2007/10/02)
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. Keywords - N-alkyl-β-hydroxyhydroxylamine; anodic oxidation; C-C bond fission; C-nitroso compound; aldehyde; oxime; azoxy compound
