Skip to main content
Log in

Electrochemical transformations of cycloheptatriene derivatives

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

Abstract

Redox reactions of a series of substituted cycloheptatrienes are studied on a platinum electrode in acetonitrile using the cyclic voltammetry method. It was found that heptaphenyl-substituted cycloheptatrienes are irreversibly oxidized in two stages in the range of high anodic potentials to form unstable radical cations and dications. As opposed to the unsubstituted and monosubstituted cycloheptatrienes, they are not reduced at the potentials higher than −2 V (SCE). A new stable radical anion was found in the reduction of N-cycloheptatrienylphthalimide. Its spin density distribution is studied by ESR spectroscopy.

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. King, R.B., Coord. Chem. Rev., 1976, vol. 20, p. 155.

    Article  CAS  Google Scholar 

  2. Jutzi, P. and Siemeling, U., J. Organomet. Chem., 1995, vol. 500, p. 175.

    Article  CAS  Google Scholar 

  3. Ceccon, A., Santi, S., Orian, L., and Bisello, A., Coord. Chem. Rev., 2004, vol. 248, p. 683.

    Article  CAS  Google Scholar 

  4. Minkin, V.I., Mikhailov, I.E., Dushenko, G.A., and Zhunke, A., Usp. Khim., 2003, vol. 72, p. 978.

    Google Scholar 

  5. Bumber, A.A., Dushenko, G.A., Profatilova, I.A., Arutyunyants, A.A., and Mikhailov, I.E., Elektrokhimiya, 2000, vol. 36, p. 622.

    Google Scholar 

  6. Plesch, P.H. and Stasko, A., J. Chem. Soc. (B), 1971, p. 2052.

  7. Zhdanov, S.I. and Frumkin, A.N., Dokl. Akad. Nauk SSSR, 1958, vol. 122, no. 3, p. 412.

    CAS  Google Scholar 

  8. Takeuchi, K., Kurosaki, T., Yokomichi, Y., Kimura, Y., Kubota, Y., Fujimoto, H., and Okamoto, K., J. Chem. Soc., Perkin Trans., 1981, no. 4, p. 670.

  9. Sioda, R.E. and Koski, W.S., J. Am. Chem. Soc., 1967, vol. 89, p. 475.

    Article  CAS  Google Scholar 

  10. Dushenko, G.A., Mikhailov, I.E., Zschunke, A., Reck, G., Shulz, B., Mugge, C., and Minkin, V.I., Mendeleev Commun., 1999, p. 222.

  11. Dushenko, G.A., Mikhailov, I.E., Mikhailova, O.I., and Minkin, V.I., Zh. Org. Chem., 2002, vol. 38, p. 1265.

    Google Scholar 

  12. Okamoto, K., Komatsu, K., Murai, O., and Sakaguchi, O., Tetrahedron Lett., 1972, vol. 13, p. 4989.

    Article  Google Scholar 

  13. Sintezy organicheskikh preparatov (Synthesis of Organic Products), Kazanskii, B.A, Ed., Moscow: Inostrannaya Literatura, 1949, vol. 2, p. 84.

    Google Scholar 

  14. Delogu, G., Faedda, G., and Gladiali, S., J. Organomet. Chem., 1984, vol. 268, p. 167.

    Article  CAS  Google Scholar 

  15. Geske, D.H., J. Am. Chem. Soc., 1959, vol. 81, p. 4145.

    Article  CAS  Google Scholar 

  16. Chao, L.S.F., Gupta, H.K., Hughes, D.W., Britten, J.F., Rigby, S.S., Bain, A.D., and McGlinchey, M.J., Organometallics, 1995, vol. 14, no. 3, p. 1139.

    Article  CAS  Google Scholar 

  17. Organic Electrochemistry, Lund H., Hammerich O., Eds., New York: Dekker, 2001.

    Google Scholar 

  18. Battiste, M., J. Am. Chem. Soc., 1961, vol. 83, p. 4101.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. A. Bumber.

Additional information

Original Russian Text © I.A. Profatilova, A.A. Bumber, I.E. Mikhailov, G.A. Dushenko, M.P. Bubnov, V. K. Cherkasov, 2008, published in Elektrokhimiya, 2008, Vol. 44, No. 7, pp. 876–881.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Profatilova, I.A., Bumber, A.A., Mikhailov, I.E. et al. Electrochemical transformations of cycloheptatriene derivatives. Russ J Electrochem 44, 812–817 (2008). https://doi.org/10.1134/S1023193508070070

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1023193508070070

Key words

Navigation