16400-86-5Relevant academic research and scientific papers
Electrochemical synthesis of nitroanilines
Gallardo, Iluminada,Guirado, Gonzalo,Marquet, Jordi
, p. 251 - 259 (2007/10/03)
Alkylamines and amides are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Useful yields (15-85%) are achieved in a simple direct and regioselective amination process. The synthetic method has been examined in the absence and presence of external bases, used to promote the first step of the nucleophilic aromatic substitution reaction, i.e. the nucleophilic attack. In both cases, good results were obtained. The unreacted starting material can easily be recovered at the end of the electrochemical oxidation process. This new method represents an environmentally favourable route to amino- and amido-substituted nitroaromatic compounds.
A Comparison of the Reactions of Some Ethyl N-Arylcarbamates with Those of the Corresponding Acetanilides. I. Nitration
Rosevear, Judi,Wilshire, John F. K.
, p. 723 - 733 (2007/10/02)
The reactions of some ethyl N-arylcarbamates and of the corresponding acetanilides towards 1 equiv. of sodium nitrate in concentrated sulfuric acid at 0-5 deg have been compared with one another and have been found to exhibit significant differences.Except in the case of the unsubstituted analogues, nitration of the carbamates was found to occur significantly more quickly than that of the acetanilides as shown by (i) a representative competitive nitration, and (ii) the fact the carbamates containing a nitro group are nitrated smoothly whereas the corresponding nitroacetanilides are slow to react.On the basis of competitive reactions, it is suggested that this difference in reactivity is due to steric factors.
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.
