INTERVENTION OF N,N-DIMETHYLANILINIUM CATION RADICAL IN THE POLONONOVSKI TYPE REACTION OF N,N-DIMETHYLANILINE N-OXIDE CATALYZED BY MESO-TETRAPHENYLPORPHINATOIRON/IMIDAZOLE

Article abstract of DOI:10.1016/S0040-4039(00)84329-4

Meso-tetraphenylporphinatoiron(III)/imidazole catalyzes the Polonovski type reaction of substituted N,N-dimethylaniline N-oxides to give mixtures of N-demethylated and N-deoxygenated products.Effect of substituent on the turnover number and the ratio of the demethylation to the deoxygenation, and other observations suggest that the Polonovski type N-demethylation reaction takes place via the rate determining N,N-dimethylanilinium cation radical formation.