Advertisement

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
Article
  • 25 Downloads

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.

Keywords

Hydrogen Spectroscopy Hydrogen Peroxide Hydroxide Organic Chemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Z. N. Nazarov and V. N. Novikov, Zh. Obshch. Khim., 31, 263 (1961).Google Scholar
  2. 2.
    V. N. Novikov and Z. N. Nazarova, Zh. Org. Khim., 2, 1901 (1966).Google Scholar
  3. 3.
    I. M. Sosonkin, T. K. Polynnikova, and G. N. Strogov, Dokl. Akad. Nauk SSSR, 218, 130 (1974).Google Scholar
  4. 4.
    I. M. Sosonkin, T. K. Polynnikova, A. Ya. Kaminskii, S. S. Gitis, A. V. Ivanov, and V. I. Kumantsov, Zh. Org. Khim., 11, 115 (1975).Google Scholar
  5. 5.
    I. M. Sosonkin, V. N. Novikov, and G. N. Strogov, Summaries of Papers Presented at the Third All-Union Conference on Charge-Transfer Complexes and Ion-Radical Salts [in Russian], Zinatne, Riga (1976), p. 94.Google Scholar
  6. 6.
    I. M. Sosonkin, G. N. Strogov, V. N. Novikov, and T. K. Ponomareva, Khim. Geterotsikl. Soedin., No. 1, 23 (1977).Google Scholar
  7. 7.
    T. Severin and H. Kulmer, Ber., 106, 1688 (1973).Google Scholar
  8. 8.
    T. Fujinaga, Y, Deguchi, and K. Umemoto, Bull. Chem. Soc. Jpn., 46, 2716 (1973).Google Scholar
  9. 9.
    G. V. Fomin, L. A. Blyumenfel'd, and B. I. Sukhorukov, Dokl. Akad. Nauk SSSR, 157, 1199 (1964).Google Scholar
  10. 10.
    G. B. Putirszkaja and I. Matus, Magy. Km. Foly., 80, 241 (1974).Google Scholar
  11. 11.
    A. Ya. Kaminskii, I. M. Sosonkin, G. N. Strogov, L. A. Gracheva, T. K. Ponomareva, and A. V. Ivanov, Zh. Org. Khim., 13, 149 (1977).Google Scholar
  12. 12.
    S. G. Mairanovskii, The Double Layer and Its Effects in Polarography [in Russian], Nauka, Moscow (1971), p. 82.Google Scholar
  13. 13.
    I. M. Sosonkin, A. N. Domarev, V. A. Subbotin, F. F. Lakomov, V. I. Kumantsov, and A. Ya. Kaminskii, Elektrokhimiya, 8, 1168 (1972).Google Scholar
  14. 14.
    R. Grigg, I. A. Knight, and M. V. Sargent, J. Chem. Soc., C, 976 (1966).Google Scholar
  15. 15.
    I. M. Sosonkin, A. N. Domarev, É. G. Kaminskaya, A. I. Tolstikov, F. F. Lakomov, and Ya. Kaminskii, Zh. Prikl. Khim., 44, 950 (1971).Google Scholar
  16. 16.
    S. G. Mairanovskii and F. S. Titov, Zh. Anal. Khim., 15, 121 (1960).Google Scholar

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

Personalised recommendations