Ozone-mediated nitratrion of arenes with nitrogen dioxide: change-over of the orienting influences of alkyl, alkoxyl and halogen substituent groups from meta to ortho-para dominance

Abstract

In ozone-mediated nitration of toluene, anisole and chlorobenzene with nitrogen dioxide, the initial products have been found to be composed mainly of the meta-nitro derivatives, but the isomer distributions are rapidly replaced by the ortho-para isomers as the reaction proceeds, sugesting the operation of the electron transfer mechanism involving the nitrogen trioxide as initial electrophile.