103427-15-2Relevant articles and documents
The Mechanism of Nitration by 4-Methyl-4-nitro-2,3,5,6-tetrabromocyclohexa-2,5-dienone
Coombes, Robert G.,Ridd, John H.
, p. 174 - 175 (1992)
Nitration of phenol by 4-methyl-4-nitro-2,3,5,6-tetrabromocyclohexa-2,5-dienone in diethyl ether is a radical process involving reaction between the phenoxyl radical and NO2 radical that has escaped from a radical pair in which it was formed by homolytic
15N-CIDNP during Photonitration of Phenol with Tetranitromethane and Reactions with Nitric and Nitrous Acid
Lehnig, Manfred,Schürmann, Klaus
, p. 913 - 918 (1998)
During the irradiation of phenol (1) with 15N-enriched tetranitromethane in acetonitrile, and during the reaction of 1 with 15N-enriched nitric acid and nitrous acid, emission due to the nitration products o- and p-nitrophenol (2a, 2b) is observed in the 15N-NMR spectra. The CIDNP effects are built up by radical pairs formed by the encounters of the radicals NO2? and 1+? or PhO?. During the reaction of 1 with nitrous acid, 2b is formed, in part due to a non-radical reaction, via oxidation of p-nitrosophenol (3).
15N NUCLEAR POLARISATION IN NITRATION AND RELATED REACTIONS. PART 2. p-NITROPHENOL
Clemens, Anthony H.,Ridd, John H.,Sandall, John P. B.
, p. 1667 - 1672 (2007/10/02)
The nitrous acid-catalysed nitration of p-nitrophenol by H(15)NO3 in aqueous trifluoroacetic acid gives a strong emission signal during reaction for the 2-(15)NO2 group in the 15N n.m.r. spectrum of the 2,4-dinitrophenol formed: the enhancement is by a factor of up to 600.The reaction is accompanied by 11percent migration of the original 4-nitro group to the 2-position and substitution by the labelled nitro group at the 4-position.The 15N n.m.r. spectrum during the related reaction using 15N labelled p-nitrophenol and unlabelled nitric acid shows that the migration of the 4-(15)NO2 group to the 2-position causes a strongly enhanced absorption signal for the 2-(15)NO2 group in the 2,4-dinitrophenol formed.A strongly enhanced absorption signal for this group is also found for the reaction of p-nitrophenol with H(15)NO3 in the presence of sodium azide.The complete set of results is interpreted in terms of nuclear polarisation deriving from the reactions of the radical pair ArO.NO2. when formed either by diffusion or from a singlet precursor.The reaction between hydrazoic acid and nitric acid is catalysed by p-nitrophenol.