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Chemistry of Heterocyclic Compounds

, Volume 24, Issue 11, pp 1238–1248 | Cite as

Mechanism and products of electrochemical reduction of 4-nitrophenyl-2,6-dimethyl-3,5-dicyano-1,4-dihydropyridines in dimethylformamide

  • L. Kh. Baumane
  • Ya. P. Stradyn'
  • R. A. Gavar
  • A. P. Gaukhman
  • G. Ya. Dubur
Article
  • 58 Downloads

Abstract

Free anion radicals of the nitrobenzene and nitrosobenzene type, which were identified by EPR spectroscopy, are formed in the electrochemical reduction of isomeric 4-(nitrophenyl)-2,6-dimethyl-3,5-dicyano-1,4-dihydropyridines on mercury and solid electrodes. Reduction of the dihydropyridine ring is observed only for N-substituted p- and m-nitrophenyl derivatives of 1,4-dihydropyridine. An intermediate with a 2-pyridonemethide structure was identified; a set of primary and secondary chemical reactions that are associated with the electrolytic reduction of the investigated compounds is presented.

Keywords

Spectroscopy Mercury Organic Chemistry Anion Radical Nitrobenzene 
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.

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Literature Cited

  1. 1.
    Ya. V. Ogle, L. Kh. Baumane, Ya. P. Stradyn', G. Ya. Dubur, V. P. Kadysh, R. A. Gavar, and V. K. Lusis, Khim. Geterotsikl. Soedin., No. 8, 1099 (1985).Google Scholar
  2. 2.
    Ya. P. Stradyn', J. Volke, L. Kh. Baumane, V. Volkova, I. Klima, G. Ya. Dubur, and R. A. Gavar, “Electrochemical reduction of 4-(nitroaryl)dihydropyridines, cyclical voltamperometry and EPR spectra of electrochemically generated anion radicals,” Preprint from the Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR (1985).Google Scholar
  3. 3.
    A. J. Bard and H. Lund, Encyclopedia of the Electrochemistry of the Elements, Vol. 13, Marcel Dekker, New York (1979).Google Scholar
  4. 4.
    A. V. Il'yasov, Yu. M. Kargin, I. D. Morozova, B. D. Chernopol'skaya, A. A. Vafina, B. V. Mel'nikov, A. S. Gel'fond, A. Sh. Mukhtarov, and Yu. G. Galyametindinov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2174 (1972).Google Scholar
  5. 5.
    EPA/NIH Mass Spectral Data Base, Vol. 1, U. S. Department of Commerce, National Bureau of Standards (1978), p. 984.Google Scholar
  6. 6.
    P. B. Ayscough, F. P. Sargent, and R. Wilson, J. Chem. Soc. B, No. 9, 903 (1966).Google Scholar
  7. 7.
    P. J. Brignell, U. Eisner, and P. G. Farrell, J. Chem. Soc. B, No. 12, 1083 (1966).Google Scholar
  8. 8.
    J. Kuthan, J. Volke, V. Volkova, and V. Simonek, Coll. Czech. Chem. Commun.,39, 3438 (1974).Google Scholar
  9. 9.
    B. A. Vigante, Ya. Ya. Ozols, M. I. Terekhova, é. S. Petrov, G. Ya. Dubur, é. é. Liepin'sh, and G. I. Rozentale, Khim. Geterotsikl. Soedin., No. 4, 491 (1986).Google Scholar
  10. 10.
    Yu. M. Kargin, N. I. Semakhina, and B. V. Mel'nikov, Zh. Obshch. Khim.,45, 401 (1975).Google Scholar
  11. 11.
    Landolt-Börnstein, Zahlenwerte und Funktionen aus Naturwissenschaften und Technik. Neue Serie, Berlin-Heidelberg-New York, Springer-Verlag (1980), Group 2, Vol. 9, Part 1, p. 576.Google Scholar
  12. 12.
    A. Z. Zandersons, V. K. Lusis, D. Kh. Mutsenietse, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 1, 81 (1987).Google Scholar
  13. 13.
    Yu. M. Kargin, V. V. Kondranina, and N. I. Semakhina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 178 (1971).Google Scholar
  14. 14.
    Ya. P. Stradyn', R. A. Gavar, and L. Kh. Baumane, Izv. Akad. Nauk Latv. SSSR, No. 2, 73 (1986).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • L. Kh. Baumane
    • 1
  • Ya. P. Stradyn'
    • 1
  • R. A. Gavar
    • 1
  • A. P. Gaukhman
    • 1
  • G. Ya. Dubur
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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