Advertisement

Fission of Activated Carbon—Nitrogen and Carbon—Sulphur Bonds. XII. Polarographic Reduction of Substituted Benzonitriles Bearing in para-Position a Carbonyl Group in Acidic Media

  • P. Zuman
  • O. Manoušek

Abstract

4-Cyanoacetophenone and 4-cyanobenzaldehyde are reduced in acid media in a four-electron step followed by a one-electrone reduction of the protonated carbonyl group. In the four-electron step the cyano group is reduced in a protonated species to methylenamino grouping. 4-Cyanobenzophenone is reduced in acid media in two two-electron steps. In the first step which is split into two one-electron waves, the carbonyl group is reduced. In the consecutive two-electron step 4-cyanobenzhydrol is further reduced.

Keywords

Cyano Group Electrolyzed Solution Drop Mercury Electrode Electrolysis Product Potential Electrolysis 
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.

References

  1. 1.
    Stackelberg M. v., Stracke W.: Z. Elektrochem. 53, 118 (1949).Google Scholar
  2. 2.
    Rjabov A. V., Panova G. D.: Dokl. Akad. Nauk SSSR 99, 547 (1954).Google Scholar
  3. 3.
    Bird L., Hale H.: Anal. Chem. 24, 586 (1952).CrossRefGoogle Scholar
  4. 4.
    Spillane L. J.: Anal. Chem. 24, 587 (1952).CrossRefGoogle Scholar
  5. 5.
    Matyska B., Klier K.: This Journal 21, 1592 (1956).Google Scholar
  6. 6.
    Claver G. C., Murphy M. E.: Anal. Chem. 31, 1682 (1959).CrossRefGoogle Scholar
  7. 7.
    Strause S. F., Dyer E.: Anal. Chem. 27, 1906 (1955).CrossRefGoogle Scholar
  8. 8.
    Bargain M.: Compt. Rend. 254, 130 (1962); 255, 1948 (1962); 256, 1990 (1963).Google Scholar
  9. 9.
    Marciszewski H.: Chem. Anal. (Warszawa) 5, 119 (1960).Google Scholar
  10. 10.
    Korsunov I. A., Vodzinskij, Ju. V., Vazanskin N. S., Kalinin A. I.: i. Obsc. Chim. 29, 1364 (1959).Google Scholar
  11. 11.
    Jarvie J. M. S., Osteryoung R. A., Janz G. J.: Anal. Chem. 28, 264 (1956).CrossRefGoogle Scholar
  12. 12.
    Volke J., Kubicek J., Santavy F.: This Journal 25, 1510 (1960).Google Scholar
  13. 13.
    Volke J., Holubek J.: This Journal 28, 1597 (1963).Google Scholar
  14. 14.
    Kardos A. M., Valenta P., Volke J.: J. Electroanal. Chem. 12, 84 (1966).CrossRefGoogle Scholar
  15. 15.
    Volke J., Kardos A. M.: This Journal 33, 2560 (1968).Google Scholar
  16. 16.
    Zuman P.: This Journal 25, 3225 (1960).Google Scholar
  17. 17.
    Zuman P., Exner O., Rekker R. F., Nauta W. T.: This Journal 33, 3213 (1968).Google Scholar
  18. 18.
    Zuman P., Horak V.: This Journal 26, 176 (1961).Google Scholar
  19. 19.
    Manousek O., Zuman P.: This Journal 29, 1432 (1964).Google Scholar
  20. 20.
    Manousek O., Zuman P.: This Journal 29, 1730 (1964).Google Scholar
  21. 21.
    Zuman P., Exner O.: This Journal 30, 1832 (1965).Google Scholar
  22. 22.
    Manousek O., Zuman P.: Chem. Commun. 1965, 158.Google Scholar
  23. 23.
    Manousek O., Exner O., Zuman P.: This Journal 33, 3979 (1968).Google Scholar
  24. 24.
    Manousek O., Zuman P.: This Journal 29, 17 (1964).Google Scholar
  25. 25.
    Nemec L., Holub I.: Unpublished results.Google Scholar
  26. 26.
    Manousek O., Exner O., Zuman P.: This Journal 33, 3988 (1968).Google Scholar
  27. 27.
    Heyrovsky M.: This Journal 28, 26 (1963).Google Scholar
  28. 28.
    Majranovskij S. G., Lisceta L. I.: This Journal 25, 3025 (1960).Google Scholar
  29. 29.
    Zuman P., Barnes D., Ryvolovâ-Kejharovâ A.: Discussions Faraday Soc. 45, 202 (1968).CrossRefGoogle Scholar
  30. 30.
    Zuman P.: This Journal 33, 2548 (1968).Google Scholar
  31. 31.
    Meites L.: Proc. XXII. Conf. IUP AC,Prague 1967, in the press.Google Scholar
  32. 32.
    Rieger P. H., Bernai I., Reinmuth W. H., Fraenkel G. K.: J. Am. Chem. Soc. 85, 683 (1963).CrossRefGoogle Scholar
  33. 33.
    Schwarz W. M., Kosower E. M., Shain I.: J. Am. Chem. Soc. 83, 3164 (1961).CrossRefGoogle Scholar
  34. 34.
    Huber W.: Z. Anal. Chem. 197, 236 (1963).CrossRefGoogle Scholar
  35. 35.
    Zuman P., Wawzonek S.: Progr. Polarography, Vol. 1, p. 303. Interscience, New York 1962.Google Scholar
  36. 36.
    Fleet B.: Private communication.Google Scholar
  37. 37.
    Zuman P.: Z. Anal. Chem. 224, 374 (1967).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Company Ltd. 1970

Authors and Affiliations

  • P. Zuman
    • 1
  • O. Manoušek
    • 1
  1. 1.J. Heyrovský Institute of PolarographyCzechoslovak Academy of SciencesPrague 1Czech Republic

Personalised recommendations