Kinetics and possible mechanisms of alkaline hydrolysis of alkoxy-NNO-azoxy compounds

Abstract

Hydrolysis rate of alkoxy-NNO-azoxy compounds like di(methoxy-NNO-azoxy)methane I, di-(methyl-NON-azoxy)formal II, di(methoxy-NNO-azoxy)methane III, and 2,2-di(methoxy-NNO-azoxy)propane IV in 5 M KOH solution was measured by manometric method at 80°C; rates relation is 1:40:540:10. Reversible deprotonation to form C-anions followed by their rapid decomposition is a presumable mechanism for compounds I–III. Nucleophilic attack of OH-anion on the carbon atom of CH3ON=N(O) group is the most probable first stage of hydrolysis in the case of compound IV.