. Aberystwyth Studies. / by Members of the University College of 4. THE ACTION OF REDUCING AGENTS ON SOME POLYNITRODIPHENYLAMINES Mono- and di-nitrodiphenylamines yield corresponding amino- derivatives on treatment with reducing agents, but in the case of the higher nitro-derivatives, condensation products of complex constitution are frequently produced. In the present work an attempt has been made to carry out the reduction of picryl- aniline () and several of its derivatives, in gradual stages. The prolonged action of alcoholic ammonium sulphide on picryl-
. Aberystwyth Studies. / by Members of the University College of 4. THE ACTION OF REDUCING AGENTS ON SOME POLYNITRODIPHENYLAMINES Mono- and di-nitrodiphenylamines yield corresponding amino- derivatives on treatment with reducing agents, but in the case of the higher nitro-derivatives, condensation products of complex constitution are frequently produced. In the present work an attempt has been made to carry out the reduction of picryl- aniline () and several of its derivatives, in gradual stages. The prolonged action of alcoholic ammonium sulphide on picryl-aniline has been found to yield phenazine, a substance which has previously been obtained by Kehrmann and Havas {Ber., 1913, 46, 347) by the nitration of phenazine and subsequent reduction of the dinitrophenazine with alcoholic ammonium sulphide. This product has also been obtained synthetically (Leeman and Grandmougin, Ber., 1908, 41, 1309 ; Kehrmann and Messinger, ibid., 1893, 26, 2373) from , by the elimination of nitrous acid, thus : /\/ \/\ /\/NH. NO a By treatment of picrylaniline with alcoholic ammonium sulphide for a limited period an intermediate product, 6-amino-diphenylamine, has been obtained. In a similar manner the reduction of picryl-p-toluidine with alcoholic ammonium sulphide has been shown to yield the corresponding phenazine derivative, the constitution of which has been confirmed by synthesis from picryl-tolylene-diamine. Picryl-m-toluidine also yields a phenazine derivative of similar type. —VOL. IV. 209 P. Please note that these images are extracted from scanned page images that may have been digitally enhanced for readability - coloration and appearance of these illustrations may not perfectly resemble the original University College of Wales (Aberystwyth, Wales). Aberystwyth : University College of Wales
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