Skip to main content
Log in

Electrogeneration of peroxodicarbonate anion: Synthesis of tetraalkylammonium silylcarboxylate

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

Abstract

Oxygen electroreduction in the presence of CO2 in acetonitrile solutions of tetraalkylammonium salts is a means to produce tetraalkylammonium peroxodicarboxylates. The latter react with triorganosilanes R3SiH to yield tetraalkylammonium salts of triorganylsilylcarboxylic acids. Diorganylsilanes under the same conditions produce cyclic siloxanes exclusively.

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. Brook, A.G., J. Am. Chem. Soc., 1955, vol. 77, p. 4827.

    Article  CAS  Google Scholar 

  2. Zhdanov, A.A., Astapov, B.A., and Dmitricheva, N.A., Zh. Obshch. Khim., 1985, vol. 55, p. 1793.

    CAS  Google Scholar 

  3. Steward, O.W., Dziedzic, J.E., and Johnson, J.S., J. Org. Chem., 1971, vol. 36, p. 3475.

    Article  CAS  Google Scholar 

  4. Brook, A.G. and Mauris, R.J., J. Am. Chem. Soc., 1957, vol. 20, p. 971.

    Article  Google Scholar 

  5. Peddle, G.J.D. and Walsingham, R.W., J. Am. Chem. Soc., 1969, vol. 91, p. 2154.

    Article  CAS  Google Scholar 

  6. Pezacki, J.P., Loncke, P.G., Ross, J.P., Warkentin, J., and Gadosy, T.A., Org. Lett., 2000, vol. 2, p. 2733.

    Article  CAS  Google Scholar 

  7. Firsova, T.P., Molodkina, A.N., Morozova, T.G., and Aksenova, I.V., Zh. Neorg. Khim., 1963, vol. 8, p. 140.

    Google Scholar 

  8. Jones, D.P. and Griffith, W.P., J. Chem. Soc., Dalton Trans., 1980, p. 2526.

  9. Roberts, J.L., Calderwood, T.S., and Sawyer, D.T., J. Am. Chem. Soc., 1984, vol. 106, p. 4667.

    Article  CAS  Google Scholar 

  10. Franchuk, I.F. and Brodskii, A.I., Dokl. Akad. Nauk SSSR, 1958, vol. 118, p. 128.

    CAS  Google Scholar 

  11. Saha, M.S., Furuta, T., and Nishiki, Y., Electrochem. Solid State Lett., 2003, vol. 6, D5–D7.

    Article  CAS  Google Scholar 

  12. Voropaev, L.E., Zharskii, I.M., Kapitsa, A.V., and Stanishevskii, V.N., Khim. Khim. Tekhnol., 1985, vol. 20, p. 43.

    CAS  Google Scholar 

  13. Filatova, L.S., Sorokina, M.F., and Khomutov, N.E., Abstracts of Papers, All-Union Conf. “Chemistry of Inorganic Peroxide Compounds,” 1973, p. 57.

  14. Saha, M.S., Furuta, T., and Nishiki, Y., Electrochem. Commun., 2004, no. 6, p. 201.

  15. Casadei, M.A., Cesa, S., Moracci, M.F., Inesi, A., and Feroci, M., J. Org. Chem., 1996, vol. 61, p. 380.

    Article  CAS  Google Scholar 

  16. Casadei M.A., Cesa, S., Feroci M., Inesi A., Rossi, L., and Moracci, F.M., Tetrahedron, 1997, vol. 53, p. 167.

    Article  CAS  Google Scholar 

  17. Casadei, M.A., Inesi, A., and Rossi, L., Tetrahedron Lett., 1997, vol. 38, p. 3565.

    Article  CAS  Google Scholar 

  18. Casadei, M.A., Micheletti, Moracci, F., Zappia, G., Inesi, A., and Rossi, L., J. Org. Chem., 1997, vol. 62, p. 6754.

    Article  CAS  Google Scholar 

  19. Johnson, E., Pool, K., and Hamm, R., Anal. Chem., 1966, vol. 38, p. 183.

    Article  CAS  Google Scholar 

  20. Sawyer, D.T., Chiericato, G., Angelis, C.T., Nanni, E.J., and Tsuchiya, T., Anal. Chem., 1982, vol. 54, p. 1720.

    Article  CAS  Google Scholar 

  21. Nicholson, R.S. and Shain, I., Anal. Chem., 1964, vol. 36, p. 706.

    Article  CAS  Google Scholar 

  22. Rudolph, M. and Feldberg, S.W., DIGISIM, release 2.1., Bioanalytical Systems Inc., 1996.

  23. Casadei, M.A., Inesi, A., Micheletti, M.F., and Rossi, L., Chem. Commun., 1996, p. 2575.

  24. Zhukov, V.V., Usp. Khim., 1997, vol. 66, p. 509.

    Google Scholar 

  25. Jouikov, V., Proc. of ISOS XIV, Wurzburg, Germany, 2005, p. 63.

  26. Jouikov, V. and Keyrouz, R., Proc., 37th Silicon Symposium, Philadelphia: USA, 2004, p. 6.

  27. Yamamoto, H., Mashino, T., Nagano, T., and Hirobe, M., Tetrahedron Lett., 1989, vol. 30, p. 4133.

    Article  CAS  Google Scholar 

  28. Bassindale, A. and Taylor, P., in The Chemistry of Organic Silicon Compounds, Patai, S. and Rappoport, Z., Eds., Chichester: Wiley, 1989, p. 895.

    Google Scholar 

  29. Simons, G., Zandler, M.E., and Talaty, E.R., J. Am. Chem. Soc., 1976, vol. 98, p. 7869.

    Article  CAS  Google Scholar 

  30. Atkins, P.W., Chimie Physique, Paris: De Boek Univ., 2000, p. 941.

    Google Scholar 

  31. Nagano, T., Yamamoto, H., and Hirobe, M., J. Am. Chem. Soc., vol. 112, p. 3529.

  32. Beachy, M.D., Cao, Y., Murphy, R.B., Perry, J.K., Pollard, W.T., Ringnalda, M.N., Vacek, G.R., Wright, J.R., Deppmeier, B.J., Driessen, A.J., Hehre, W.J., Johnson, J.A., Klunzinger, P.E., Watanabe, M., and Yu, J., TITAN, release 1.07, Wavefunction Inc./Schroedinger Inc., 1999–2003.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. V. Jouikov.

Additional information

Original Russian Text © K.N. Singh, S.Neuhold, C.Grogger, V.V. Jouikov, 2007, published in Elektrokhimiya, 2007, Vol. 43, No. 10, pp. 1234–1238.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singh, K.N., Neuhold, S., Grogger, C. et al. Electrogeneration of peroxodicarbonate anion: Synthesis of tetraalkylammonium silylcarboxylate. Russ J Electrochem 43, 1170–1174 (2007). https://doi.org/10.1134/S1023193507100102

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1023193507100102

Key words

Navigation