95192-59-9Relevant articles and documents
Synthetic utilization of polynitroaromatic compounds. 3. Preparation of substituted dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-trinitrobenzoic acid via nucleophilic displacement of nitro groups
Samet, Alexander V.,Marshalkin, Victor N.,Kislyi, Konstantine A.,Chernysheva, Natalya B.,Strelenko, Yuri A.,Semenov, Victor V.
, p. 9371 - 9376 (2007/10/03)
1,3-Dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro group
Substituent Effects on the Decarboxylation of Dinitrobenzoate Ions, Representative Aromatic SE1 Reactions
Segura, Pascual,Bunnett, Joseph F.,Villanova, Laura
, p. 1041 - 1045 (2007/10/02)
Kinetics of decarboxylation, in water solution, of several 4-substituted 2,6-dinitrobenzoic and 2-substituted 4,6-dinitrobenzoic acids were determined, at several temperatures.The reactions are first order at the low concentrations employed, at which the acids are fully dissociated.Decarboxylation is accelerated by electron-attracting substituents; the Hammett ρ for the effects of 4-substituents is about +2.6.All the decarboxylations involve large positive enthalpies and entropies of activation.The solvent kinetic isotope effect (D2O/H2O) is not significantly different from unity.The data support a mechanism where in the substituted benzoate ion loses CO2 in the rate-determining step, forming a substituted aryl anion, which is then rapidly hydronated by the solvent.In the case of 2-methoxy-4,6-dinitrobenzoate ion, reaction occured with strikingly different activation parameters.