Abstract
The reduction of 2-bromo-5-nitrothiophene and 2-iodo-5-nitrothiophene in dimethylformamide (DMF) was studied by means of classical and commutated polarography, EPR spectroscopy, a rotating platinum disk electrode with a ring, and preparative electrolysis. It was established that, depending on the nature of the halogen, their anion radicals may undergo further reduction to 2-nitrothiophene anion radicals or decomposition with splitting out of a halide anion and conversion to nitrothienyl radicals, which were identified on the ring electrode. The latter are capable of undergoing dimerization to 2,2′-dinitro-5,5′-dithienyl. The spectra of the anion radicals of 2-nitrothiophene and 2,2′-dinitro-5,5′-dithienyl were recorded by means of EPR. A mechanism for the reduction of halonitrothiophenes is proposed.
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