21985-87-5Relevant articles and documents
REACTIONS OF PENTANITROANILINE WITH MONOHYDRIC ALCOHOLS
Kanakina, T. P.,Golod, E. L.,Shugalei, I. V.,Bazanov, A. G.,Tselinskii, I. V.
, p. 481 - 487 (2007/10/02)
The course of reaction between pentanitroaniline and monohydric alcohols is determined by the structure of the alcohol. The reactions of primary and secondary alcohols with pentanitroaniline give 3-alkoxy-2,4,5,6-tetranitroanilines as major products. The reactions of pentanitroaniline with tertiary alcohols give 5-amino-2,3,4,6-tetranitrophenol as the sole product. The reactions of pentanitroaniline with monohydric alcohols proceed through the intermediate formation of a charge-transfer complex and can be treated in terms of a single mechanism both with primary and secondary and with tertiary alcohols.
Synthesis of Polynitro Compounds. Hexasubstituted Benzenes
Atkins, Ronald L.,Hollins, Richard A.,Wilson, William S.
, p. 3261 - 3266 (2007/10/02)
The synthesis of the three isomeric aminotetranitrotoluenes by nitration of an appriopriate aminodinitrotoluene is presented, and the apparent ipso nitration of 4-amino-2,6-dinitrotoluene to give pentanitroaniline, is also discussed.The oxidation of the isomeric aminotetranitrotoluenes to pentanitrotoluene is described, as is the ammonolysis of pentanitroaniline and of pentanitrotoluene.
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.