62285-55-6Relevant academic research and scientific papers
HYDROGEN ABSTRACTION FROM THE ISOMERIC CYMENES
Sulpizio, A.,Mella, M.,Albini, A.
, p. 7545 - 7552 (2007/10/02)
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.
THE ROLE OF NITRATE FREE RADICALS IN THE PHOTOCHEMICAL SIDE-CHAIN NITROOXYLATION OF ALKYLBENZENES BY CERIUM(IV) AMMONIUM NITRATE IN ACETONITRILE
Baciocchi, E.,Giacco, T. Del,Rol, C.,Sebastiani, G. V.
, p. 541 - 544 (2007/10/02)
It is suggested that the reactive species in the CAN-induced photochemical side-chain nitrooxylation of alkylbenzenes is the nitrate radical, which probably acts as one-electron oxidant.
TWO-PHASE OXIDATION OF SOME AROMATIC COMPOUNDS WITH CERIUM AMMONIUM NITRATE IN THE PRESENCE OF SURFACTANTS.
Skrzewski,Cichacz
, p. 271 - 274 (2007/10/02)
The two-phase oxidations of 3,6-dimethoxydurene and xylenes in cyclohexane solutions with the aqueous solution of cerium ammonium nitrate were carried out in the presence of cationic, nonionic, and anionic surfactants. Both cationic (ammonium salt) and nonionic (Dipodand) surfactants inhibited the reaction. The anionic surfactant (sodium dodecyl sulfate, SDS) catalyzed these oxidations. From the product distribution it was concluded that the catalytic action of SDS is due to the binding of aromatic compounds and the Ce(IV) ions to the surface of the SDS micelles. The micellar oxidant has the high oxidation potential which should allow to oxidize the comparatively nonreactive substrates.
PHOTOCHEMICAL NITROOXYLATION OF METHYLBENZENES BY CERIUM(IV) AMMONIUM NITRATE IN ACETONITRILE
Baciocchi, E.,Rol, C.,Sebastiani, G. V.,Serena, B.
, p. 1945 - 1946 (2007/10/02)
The photochemical reaction of substituted toluenes with CAN in CH3CN leads to good yields of benzyl nitrates under very mild conditions.
Reactions of Cerium(IV) Ammonium Nitrate with Aromatic Compounds in Acetonitrile. Part 1. The Mechanism of Side-chain Substitution
Dinctuerk, Suphi,Ridd, John H.
, p. 961 - 964 (2007/10/02)
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 10>-p-xylene suggests that proton loss from this radical cation is, at least partly, rate-determining.
