Anodic Oxidation of Amines. VII. Oxidation of β-Alkanolamines in Aqueous Buffer of pH 10

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The anodic oxidation of several different types of β-alkanolamines, R^1R^2C (OH) CR^3R^4NR^5R^6,was studied by cyclic voltammetry and controlled potential electrolysis in an aqueous carbonate buffer of pH 10 at a glassy carbon electrode. Upon oxidation, both the (α) C-(β) C and the C-N bonds are cleaved. Substituents R^1-R^4 affect the first oxidation potential and product distribution. The relative rates of the bond cleavages were estimated from the oxidation products. It was found that most of the amine cleaves through the (α) C-(β) C bond when at least one of the R groups is phenyl, nearly half cleaves through this bond when R is alkyl, and only about a tenth does so when R^1-R^4 are all hydrogen. The stability of the transient intermediates at the e-c step of the e-c-e process seems to affect the oxidation potentials and to govern the relative rates of the (α) C-(β) C bond cleavage. A scheme for the reaction processes is proposed.
1982-04-25