Journal of the Chemical Society. Perkin transactions II p. 961 - 964 (1982)
Update date:2022-08-31
Topics:
Dinctuerk, Suphi
Ridd, John H.
Benzene, alkylbenzenes, and phenolic ethers react with cerium(IV) ammonium nitrate in acetonitrile to give nitrocompounds and (if α-hydrogen atoms are present) also the products of side-chain substitution.With many substrates, the major products of side-chain substitution are benzyl nitrates but compounds which can give rise to particularly stable benzyl cations give mainly products from reaction with the solvent.Relative rates of side-chain substitution have been determined by the competition method: the results indicate reaction via a radical cation and the isotope effect kH/kD=2.3 observed in reactions with <2H10>-p-xylene suggests that proton loss from this radical cation is, at least partly, rate-determining.
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