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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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 195–198, February, 1981.
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Sosonkin, I.M., Strogov, G.N., Ponomareva, T.K. et al. Mechanism of the electrochemical reduction of 2-halo-5-nitrothiophenes in dimethylformamide. Chem Heterocycl Compd 17, 137–140 (1981). https://doi.org/10.1007/BF00507243
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DOI: https://doi.org/10.1007/BF00507243