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Mechanism of halogen substitution in the electrochemical reduction of halonitrofurans in dimet hylformamide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The polarographic reduction of 2-halo-5-nitrofurans in dimethylformamide, which leads ultimately to replacement of the halogen by hydrogen to give a nitrofuran, was studied. The ESR spectra of halonitrofuran anion radicals (Hal=Cl, Br) were recorded. Only the spectrum of the nitrofuran anion radical can be observed in the reduction of 2-I-5-nitrofuran. It is shown that the stabilities of the anion radicals of the halonitrofurans and the mechanism of their subsequent transformations depend to a considerable degree on the nature of the halogen.

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Authors and Affiliations

  1. Rostov State University, 344006, Rostov-on-Don

    I. M. Sosonkin, G. N. Strogov, V. N. Novikov & T. K. Ponomareva

  2. All-Union Scientific-Research and Design Institute of Monomers, 300026, Tula

    I. M. Sosonkin, G. N. Strogov, V. N. Novikov & T. K. Ponomareva

Authors
  1. I. M. Sosonkin
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  2. G. N. Strogov
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  3. V. N. Novikov
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  4. T. K. Ponomareva
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 23–26, January, 1977.

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Sosonkin, I.M., Strogov, G.N., Novikov, V.N. et al. Mechanism of halogen substitution in the electrochemical reduction of halonitrofurans in dimet hylformamide. Chem Heterocycl Compd 13, 18–21 (1977). https://doi.org/10.1007/BF00479860

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  • DOI: https://doi.org/10.1007/BF00479860

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