Abstract
The electrohydrogenation of 2-iodonitrobenzene at mercury and Raney metal electrodes (R-Ni, R-Co and D-Cu) was studied in aqueous methanolic solutions. Four different media were used: a basic KOH medium (pH > 13), a neutral acetate buffered medium (pH 7) and two media containing a pyridine buffer (pH 3 and pH 10). Cyclic voltammetric reductions were carried out at mercury, bright nickel and bright copper cathodes. The product distribution of preparative-scale electrolyses at a mercury pool cathode was compared with that of electrohydrogenation at Raney metal electrodes and of catalytic hydrogenation (open-circuit experiments) at Raney metals. Electrohydrogenation at R-Co and D-Cu electrodes gave 2-iodoaniline with high selectivity ( ⩾ 94%). The results are discussed in the light of the various mechanistic pathways.
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