Unusual isomer distribution of dinitrobenzenes and nitrophenols formed as side products during the ozone-mediated nitration of benzene with nitrogen dioxide. Further evidence for the alternative mechanism of electrophilic nitration of arenes

Abstract

Dinitrobenzenes and nitrophenols formed as side products in the title reaction leading to nitrobenzene show an isomer distribution that is significantly different from those observed in the conventional nitration using nitric acid or nitric acid–sulfuric acid, suggesting the operation of a non-classical nitration mechanism involving nitrogen trioxide as the initial electrophile.