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Role of electron transfer in reactions involving substitution of halogen in 2-halo-5-nitrofurans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The replacement of the halogen in 2-halo-5-nitrofurans (Hal=C1, Br, I) in dimethylformamide (DMF) under the influence of tetra-n-butylammonium hydroxide to give 2-hydroxy-5-nitrofuran salts was studied. The intermediate anion radicals of the halonitrofurans were recorded by EPR spectroscopy; bromo- and iodonitrofurans can give 5,5′-dinitro-2,2′-difuryl anion radicals under the influence of Bu4NOH. The polarographic reduction of halonitrofurans in the presence of hydrogen peroxide also leads to 2-hydroxy-5-nitrofuran. A mechanism for the transformation is proposed.

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Authors and Affiliations

  1. Rostov State University, 344711, Rostov-on-Don

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

  2. All-Union Scientific-Research and Planning 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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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1604–1607, December, 1979

Original article submitted March 17, 1977; revision submitted October 30, 1978.

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Sosonkin, I.M., Strogov, G.N., Novikov, V.N. et al. Role of electron transfer in reactions involving substitution of halogen in 2-halo-5-nitrofurans. Chem Heterocycl Compd 15, 1284–1287 (1979). https://doi.org/10.1007/BF00514726

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  • DOI: https://doi.org/10.1007/BF00514726

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