Oxidative Bond Fission of β-Alkanolamines by Chlorine Dioxide and the Effect of an Oxymethylene Group at the β-Carbon on the Reaction

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Oxidative bond fission of β-alkanolamines, R¹R²C (OH) CR³₂NHR⁴ (group A amines) and R⁵-O-CH₂CH (OH)-CH₂NHR⁶ (group B amines) by chlorine dioxide was studied in buffer solution of pH 10, and the results were compared with those obtained by electrochemical oxidation of group A amines. No significant difference was found between the two groups of amines, and the fission mainly occurred at the C-N rather than the (α) C-(β) C bond except in the case of the amine in which R¹=phenyl. Chlorine dioxide oxidation, in general, caused more C-N bond fission than electrochemical oxidation did, and the reason for this is discussed.