HYDROGEN ABSTRACTION FROM THE ISOMERIC CYMENES

Article abstract of DOI:10.1016/S0040-4020(01)89216-4

The irradiation of cerium (IV) ammonium nitrate in the presence of ortho, meta and para cymene yields products from attack at the methyl group (the nitrates - these ones in 55 to 69percent isolated yield-, the nitro derivatives, and the aldehydes) as well as at the isopropyl group (the acetophenones, not obtained from the ortho isomer), with minimal ring nitration.The formation of bibenzyls on irradiation with t-butyl peroxide of the same substrates is also studied.The mechanisms of the reactions with the NO3 radical, a good electron acceptor, and with the alkoxy radical are contrasted and compared with photochemical hydrogen abstraction by n?* and, respectively, ??* excited states.