Superoxide Anion Efficiently Performs the Oxidative Cleavage of C=NOH Bonds of Amidoximes and N-hydroxyguanidines with Formation of Nitrogen Oxides

Article abstract of DOI:10.1016/0040-4039(95)01242-A

Potassium superoxide stoechiometrically reacts with arylamidoximes with the selective formation of the corresponding benzamide and nitrogen oxides (mainly NO2^-) in high yield.A similar oxidative cleavage of the C=NOH bond of N-hydroxy-arylguanidines also occurs upon reaction with KO2; the yield of the corresponding urea is lower and large amounts of the corresponding cyanamide are also formed.The significance of this reaction of O2^.- with compounds containing a C=NOH bond in the biological formation of nitrogen oxides including NO is discussed.