A NOVEL BASE-CATALYZED TRANSFORMATION OF α-AZOBENZYL HYDROPEROXIDE INTO BENZOIC ACID. A POSTULATED OXENOID INTERMEDIATE OF THE REACTION.

Article abstract of DOI:10.1016/S0040-4039(00)88108-3

α-Azobenzyl hydroperoxide (1) gives benzoic acid, 4-bromophenyl-pyridines (2 and 3) in addition to benzoyldiazene (4) and benzohydrazide (5) in the reaction catalyzed by pyridine; dioxirane (9) or carbonyl oxide (10) is proposed as an intermediate.