Russian Chemical Bulletin

, Volume 46, Issue 3, pp 599–602 | Cite as

Electrochemical oxidation of malonic esters in acetonitrile in the presence of iodides as mediators

  • S. K. Fedukovich
  • M. N. Elinson
  • G. I. Nikishin
Brief Communications
  • 43 Downloads

Abstract

Electrochemical oxidation of malonic esters in acetonitrile in the presence of iodides follows two different pathways depending on the nature of the cation. In the presence of Lil, alkyl 1,1,2,2,3,3-propanetetracarboxylates were obtained in 85–98% yields. In the presence of Nal, Kl, or Bu4NI, the formation of 1,1,2,2-ethanetetracarboxylates and their subsequent dehydrogenation to ethenetetracarboxylates was the main reaction pathway.

Key words

electrochemical oxidation malonic ester mediators esters of polycarboxylic acids 

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References

  1. 1.
    S. P. Mulliken,Am. Chem. J., 1893,15, 523.Google Scholar
  2. 2.
    R. Brettle and D. Seddon,J. Chem. Soc.,C., 1970, 1153.Google Scholar
  3. 3.
    M. N. Elinson, S. K. Fedukovich, and G. I. Nikishin,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2534 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988,37, 2285 (Engl. Transl.)].Google Scholar
  4. 4.
    M. N. Elinson, S. K. Fedukovich, and G. I. Nikishin,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 352 [Bull. Acad. Sci. USSR, Div. Chem. Sci. 1989,38, 301 (Engl. Transl.)].Google Scholar
  5. 5.
    G. I. Nikishin, M. N. Elinson, and S. K. Fedukovich,Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1919 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986,35, 1749 (Engl. Transl.)].Google Scholar
  6. 6.
    T. Okubo and S. Tsutsumi,Bull. Chem. Soc. Jap., 1964,37, 1794.CrossRefGoogle Scholar
  7. 7.
    E. M. Arnett, S. G. Maroldo, S. L. Schilling, and J. A. Harrelson,J. Am. Chem. Soc., 1984,106, 6759.CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • S. K. Fedukovich
    • 1
  • M. N. Elinson
    • 1
  • G. I. Nikishin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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