SUPEROXIDE ANION EFFICIENTLY PERFORMS THE OXIDATIVE CLEAVAGE OF C=NOH BONDS OF AMIDOXIMES AND N-HYDROXYGUANIDINES WITH FORMATION OF NITROGEN-OXIDES

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 O-2(.-) with compounds containing a C=NOH bond in the biological formation of nitrogen oxides including NO is discussed.