Skip to main content
Log in

Electroreduction of Nitriles: The Reduction of Furfurylidene- and Benzylidenemalonodinitriles and Esters of Substituted 1-Cyanoacrylic Acids

  • Published:
Russian Journal of Electrochemistry Aims and scope Submit manuscript

Abstract

The electrochemical reduction of compounds with a common formula R1(H)C=C(CN)R2, where R1 is C6H5, n-CH3OC6H4, n-FC6H4, or α-furyl; and R2 is CN or COOC2H5 is studied. The reduction of these compounds at a zinc cathode in the water–acetonitrile KH2PO4 solution yields both cyclic and linear hydrodimers. The relative yield of the linear hydrodimer increases with lowering the temperature and acetonitrile content in the catholyte. The obtained data well correlate with the suggestion that the cyclic products form in the catholyte bulk from linear hydrodimers.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Smirnov, Yu.D., Smirnov, S.K., and Tomilov, A.P., Zh. Org. Khim., 1973, vol. 9, p. 913.

    Google Scholar 

  2. Avaca, L.A. and Utley, J.H.P., J. Chem. Soc., Perkin Trans. 1, 1975, p. 971.

  3. Avaca, L.A. and Utley, J.H.P., J. Chem. Soc., Perkin Trans. 2, 1975, p. 161.

  4. Smirnov, Yu.D., Tomilov, A.P., and Smirnov, S.K., Zh. Org. Khim., 1975, vol. 11, p. 522.

    Google Scholar 

  5. von Becker, H.G.O., Berger, W., Domschke, G., et al., Organikum: Organisch-chemisches Grundpraktikum, vol. 2, Wiley-VCH, Weinheim, 2001.

  6. Corson, B.B. and Stoughton, R.W., J. Am. Chem. Soc., 1928, vol. 50, p. 2825.

    Google Scholar 

  7. Hinrichsen, H. and Lonsen, O., Ann. Chem., 1951, vol. 336, p. 344.

    Google Scholar 

  8. Jessen, H.J., Ber. Bunsen-Ges. Phys. Chem., 1906, vol. 39, p. 4089.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tomilov, A.P., Chernykh, I.N. Electroreduction of Nitriles: The Reduction of Furfurylidene- and Benzylidenemalonodinitriles and Esters of Substituted 1-Cyanoacrylic Acids. Russian Journal of Electrochemistry 39, 1197–1200 (2003). https://doi.org/10.1023/B:RUEL.0000003445.59218.a3

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUEL.0000003445.59218.a3

Navigation