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The electrolytic reduction of paranitro compounds in sulphuric acid solution

Noyes, Arthur A. and Dorrance, John T. (1895) The electrolytic reduction of paranitro compounds in sulphuric acid solution. Journal of the American Chemical Society, 17 (11). pp. 855-859. ISSN 0002-7863. doi:10.1021/ja02166a005.

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It was shown some time ago by Noyes and Clement that nitrobenzene in sulphuric acid solution is transformed by electrolytic hydrogen into paraamidophenolsulphonic acid. It has since been proved by the extended investigations of Gattermann and his students that this behavior is characteristic of aromatic nitro compounds in general, one of the oxygen atoms of the nitro group always migrating during the reduction to the para position with the production of a hydroxyl group. It is evident, however, that this cannot take place when the position para to the nitro group is occupied by another element or group than hydrogen. The purpose of our investigation was to determine the nature of the reduction-products of a number of such compounds with the view of ascertaining any general principle that may exist. Only three such para compounds have been previously studied, namely, paranitrotoluene and paranitroorthotoluidine by Gattermann and paraiiitrobenzoic acid by Noyes and Clement. We have tiow investigated three additional ones, paranitraniline, paranitrophenol, and parachlornitrobenzene.

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Additional Information:© 1895 American Chemical Society. Received September 9, 1895.
Issue or Number:11
Record Number:CaltechAUTHORS:20161018-164858898
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Official Citation:THE ELECTROLYTIC REDUCTION OF PARANITRO COMPOUNDS IN SULPHURIC ACID SOLUTION.1 Arthur A. Noyes and John T. Dorrance Journal of the American Chemical Society 1895 17 (11), 855-859 DOI: 10.1021/ja02166a005
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:71246
Deposited By: George Porter
Deposited On:19 Oct 2016 16:19
Last Modified:11 Nov 2021 04:42

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