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

Oxidative bond fission of β-alkanolamines, R^1R^2C (OH) CR^3_2NHR^4 (group A amines) and R^5-O-CH_2CH (OH)-CH_2NHR^6 (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 R^1=phenyl. Chlorine dioxide oxidation, in general, caused more C-N bond fission than electrochemical oxidation did, and the reason for this is discussed.