Skip to main content
SpringerLink
Log in

Electrochemical Reduction of 1,4-Disubstituted Phthalazines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Electrochemical reduction in dimethylformamide of unsymmetrical 1-Cl-4-X-phthalazines and symmetrical 1,4-X2-phthalazines (X = Cl, PhO, MeO, EtO, i-PrO) was studied by voltammetry and electrolysis-ESR. The electron trasfer on 1,4-dichlorophthalazine and unsymmetrical 1-Cl-4-X-phthalazines induces anionoid elimination of Cl and X, pyridazine ring cleavage, and phthalonitrile formation. In this previously unknown process the transfer of two electrons induces cleavage of three σ bonds and formation of two new π bonds. The reduction of 1,4-dialkoxy(diaryloxy)phthalazines involves formation of stable radical anions which undergo no heteroring cleavage. Possible mechanisms of the processes studied were discussed. It was assumed that the same mechanism with pyridazine ring cleavage may be realized with other phthalazine derivatives and heteroannelated pyridazines containing readily leaving nucleofuge groups α to nitrogens.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Plump, R.E. and Hammet, L.P., Trans. Electrochem. Soc., 1938, vol. 73, Chem. Abstr., 1938, vol. 32, no. 7, no. 24 368.

  2. Butin, K.P., Usp. Khim., 1971, vol. 40, no. 6, p. 1058.

    Google Scholar 

  3. Berdnikov, E.A., Fedorov, S.B., and Kargin, Yu.M., Zh. Obshch. Khim., 1978, vol. 48, no. 4, p. 875.

    Google Scholar 

  4. Chechina, O.N. and Tomilov, A.P., Elektrokhimiya, 1999, vol. 35, no. 2, p. 149.

    Google Scholar 

  5. Taran, L.A., Buzykin, B.I., Mironova, O.Yu., Gazetdinova, N.G., and Kitaev, Yu.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1983, no. 1, p. 166.

  6. Sosonkin, I.M., Strogov, G.N., Novikov, V.N., and Ponomareva, T.K., Khim. Geterotsikl. Soedin., 1977, no. 1, p. 23.

  7. Sosonkin, I.M., Strogov, G.N., Ponomareva, T.K., Domaraev, A.N., Glushkova, A.A., and Freidlin, G.N., Khim. Geterotsikl. Soedin., 1981, no. 2, p. 195.

  8. Alwair, K. and Grimshaw, J., J. Chem. Soc., Perkin Trans. 2, 1973, no. 13, p. 1811.

  9. Fuchs, P., Hess, U., Holst, H.H., and Lund, H., Acta Chem. Scand., 1981, no. 3, p. 185.

  10. Sosonkin, I.M. and Strogov, G.N., Khim. Geterotsikl. Soedin., 1982, no. 8, p. 1126.

  11. Shimanskaya, N.P., Kotok, L.A., and Alekhina, T.F., Zh. Obshch. Khim., 1976, vol. 46, no. 10, p. 2346.

    Google Scholar 

  12. Khmel'nitskaya, E.Yu., Zh. Obshch. Khim., 1977, vol. 47, no. 5, p. 1158.

    Google Scholar 

  13. Supin, G.S., Fainshraiber, M.Ya., Mel'nikova, I.A., Mel'nikov, I.A., and Motorova, T.N., Zh. Obshch. Khim., 1977, vol. 47, no. 10, p. 2338.

    Google Scholar 

  14. Ivanova, V.Kh., Buzykin, B.I., and Bystrykh, N.N., Khim. Geterotsikl. Soedin., 1979, no. 4, p. 541.

  15. Buzykin, B.I., Yanilkin, V.V., Morozov, V.I., Maksimyuk, N.I., and Eliseenkova, R.M., Abstracts of Papers, Mezhdunarodnaya Nauchnaya Konferentsiya “Organicheskii sintez i kombinatornaya khimiya” (Int. Sci. Conf. “Organic Synthesis and Combinatorial Chemistry”), Moscow, 1999, P-27.

  16. Buzykin, B.I., Yanilkin, V.V., Morozov, V.I., Maksimyuk, N.I., Eliseenkova, R.M., and Nastapova, N.V., Mendeleev. Commun., 2000, no. 1, p. 34.

  17. Buzykin, B.I., Yanilkin, V.V., Morozov, V.I., Eliseenkova, R.M., and Maksimyuk, N.I., Izv. Ross. Akad. Nauk, Ser. Khim., 2000, no. 1, p. 181.

  18. Stone, E.W. and Maki, A.H., J. Chem. Phys., 1963, vol. 39, no. 7, p. 1635.

    Google Scholar 

  19. Wiberg, K. and Lewis, Th.P., J. Am. Chem. Soc., 1970, vol. 92, no. 24, p. 7154.

    Google Scholar 

  20. Lund, H. and Jensen, E.Th., Acta Chem. Scand., 1970, vol. 24, no. 6, p. 1867.

    Google Scholar 

  21. Rieger, P.H., Bernal, J., Reinmuth, W.H., and Fraenkel, G.K., J. Am. Chem. Soc., 1963, vol. 85, no. 6, p. 683.

    Google Scholar 

  22. Mann, C.K. and Barnes, K.K., Electrochemical Reactions in Nonaqueous Media, New York: Dekker, 1970. Translated under the title Elektrokhimicheskie reaktsii v nevodnykh sistemakh, Moscow: Khimiya, 1974, p. 194.

    Google Scholar 

  23. Mairanovskii, V.G., Elektrosintez monomerov (Electrosynthesis of Monomers), Moscow: Nauka, 1980, p. 244.

    Google Scholar 

  24. Buzykin, B.I., Bystrykh, N.N., Stolyarov, A.P., Flegontov, S.A., Zverev, V.V., and Kitaev, Yu.P., Khim. Geterotsikl. Soedin., 1976, no. 3, p. 402.

  25. Cook, J.C.S., Katrizkiy, A.R., Page, A.D., and Ramaian, M., J. Chem. Soc., Perkin Trans. 2, 1973, no. 9, p. 1184.

  26. Mairanovskii, V.G., Dokl. Akad. Nauk SSSR, 1985, vol. 284, no. 2, p. 386.

    Google Scholar 

  27. Yanilkin, V.V., Doctoral (Chim.) Dissertation, Kazan, 1998.

  28. Yanilkin, V.V., Berdnikov, E.A., and Buzykin, B.I., Elektrokhimiya, 2000, vol. 36, no. 2, p. 146.

    Google Scholar 

  29. Druey, J. and Ringer, B.H., Helv. Chim. Acta, 1951, vol. 34, no. 21, p. 195.

    Google Scholar 

  30. Rowe, F.M. and Peters, A.T., J. Chem. Soc., 1933, p. 1331.

  31. Elvidge, J.A. and Redman, A.P., J. Chem. Soc., 1960, no. 4, p. 1710.

  32. Braun, A. and Tcherniac, J., Ber., 1907, no. 40, part 2, p. 2709.

Download references

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    V. V. Yanilkin, B. I. Buzykin, V. I. Morozov, N. V. Nastapova, N. I. Maksimyuk & R. M. Eliseenkova

Authors
  1. V. V. Yanilkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. I. Buzykin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Morozov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Nastapova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. I. Maksimyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. R. M. Eliseenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yanilkin, V.V., Buzykin, B.I., Morozov, V.I. et al. Electrochemical Reduction of 1,4-Disubstituted Phthalazines. Russian Journal of General Chemistry 71, 1636–1646 (2001). https://doi.org/10.1023/A:1013979709884

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1013979709884

Keywords

Search

Navigation