Chemistry of Heterocyclic Compounds

, Volume 15, Issue 12, pp 1284–1287 | Cite as

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

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


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.


Hydrogen Spectroscopy Hydrogen Peroxide Hydroxide Organic Chemistry 
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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • I. M. Sosonkin
    • 1
    • 2
  • G. N. Strogov
    • 1
    • 2
  • V. N. Novikov
    • 1
    • 2
  • T. K. Ponomareva
    • 1
    • 2
  1. 1.Rostov State UniversityRostov-on-Don
  2. 2.All-Union Scientific-Research and Planning Institute of MonomersTula

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