3698-53-1Relevant articles and documents
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Crampton,M.R.,El Ghariani,M.
, p. 391 - 395 (1970)
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Synthesis of Polynitrobenzenes. Oxidation of Polynitroanilines and Their N-Hydroxy, N-Methoxy, and N-Acetyl Derivatives
Atkins, Ronald L.,Nielsen, Arnold T.,Bergens, Cynthia,Wilson, William S.
, p. 503 - 507 (2007/10/02)
Nitro-substituted arylhydroxylamines and alkyloxyamines have been oxidized to polynitroaryl compounds by utilizing ozone.Polynitroanilines have been oxidized to polynitroaromatics by peroxydisulfuric acid generated in situ from SO3 and ozone.Thus N-hydroxy-2,4,6-trinitroaniline (1a) or N-methoxy-2,4,6-trinitroaniline (1b) was cleanly oxidized to 1,2,3,5-tetranitrobenzene (2) by reaction with ozone in methylene chloride.Weakly basic amines such as pentanitroaniline (10) can conveniently be oxidized to hexanitrobenzene (11) in high yields by simply dissolving the amine in oleum and introducing ozone.A variety of substituted arylamines have been oxidized to polynitroaromatic compounds by using these two oxidation techniques.
ACTION OF NITRIC ACID ON 2,4,6-TRINITROPHENYL ARENE AND ALKANECARBOTHIOATES
Nurgatin, V. V.,Sharnin, G. P.,Savel'eva, L. A.,Nurgatina, R. B.
, p. 2167 - 2169 (2007/10/02)
For the case of the reaction of S,S'-bis(2,4,6-trinitrophenyl)dithiooxalate with concentrated nitric acid it was found that the sulfur-containing groups in the esters of thiocarboxylic acids are substituted by hydroxy and nitroso groups.The reaction, which is accompanied by copious release of nitrogen oxides and increase in temperature, leads to 2,4,6-trinitrophenol or 2,4,6-trinitronitrosobenzene.The structure of the latter was confirmed by IR and UV spectroscopy and by oxidation to 1,2,3,5-tetranitrobenzene. 2,4,6-Trinitrophenyl benzenecarbothioates give the nitroderivative only when the acids contain not more than one nitro group in the phenyl radical.The nitroso group in 2,4,6-trinitronitrosobenzene, like the halogen in picryl halides, is readily substituted by the action of nucleophilic reagents.
