The electrolytic reduction of paranitro compounds in sulphuric acid solution

Abstract

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.