Observation on the Fragmentation of Some Tosylhydrazones Using Electrochemically Generated Superoxide Ion

Abstract Superoxide ion (O2\ewdot) generated in situ by electrochemical reduction of molecular oxygen in dimethylformamide (DMF) at mercury cathode, behaves as a mild effective base to deprotonate the acidic hydrogen from tosylhydrazones of benzophenone (1), benzaldehyde (2), cyclohexanone (3), benzoin (4), acetophenone (5), and benzil (6) finally affording tetraphenylethene (1a), trans-stilbene (2a), cyclohexene (3a), deoxybenzoin (4a), acetophenone azine (5a), and 4,5-diphenyl-1-tosylamino-1,2,3-triazole (6a) respectively in good to excellent yield.