OZONE-MEDIATED NITRATION OF ARENAS WITH NITROGEN-DIOXIDE - CHANGE-OVER OF THE ORIENTING INFLUENCES OF ALKYL, ALKOXYL AND HALOGEN SUBSTITUENT GROUPS FROM META TO ORTHO-PARA DOMINANCE

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 ar e rapidly replaced by the ortho-pal-a isomers as the reaction proceeds , suggesting the operation of the electron transfer mechanism involvin g the nitrogen trioxide as initial electrophile.