Skip to main content
Log in

Electrolysis of Nitro Compound Salts: Application in Ketone Synthesis

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

Abstract

One-pot electrochemical method of synthesis of ketones, diketones, and esters of monoketo- and diketoalkanoic acids is elaborated. This method is based on the diaphragmless galvanostatic electrolysis of Na salts of secondary nitro compounds—derivatives of nitrohydrocarbons, nitroketones, and esters of nitrated alkanoic acids—in methanol.

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. Nef, J.U., Ann., 1894, vol. 280, p. 263.

    Google Scholar 

  2. Noland, W.E., Chem. Rev., 1955, vol. 55, p. 137; Patrick, H.W., Org. React., 1990, vol. 38, p. 665.

    Google Scholar 

  3. Shechter, H. and Williams, F.T., J. Org. Chem., 1962, vol. 27, p. 3699; Freeman, F. and Lin, D.K., J. Org. Chem., 1971, vol. 36, p. 1335.

    Google Scholar 

  4. Ballini, R., Bosica, G., and Gigli, F., Tetrahedron, 1998, vol. 54, p. 7573.

    Google Scholar 

  5. Pagano, A.H. and Shechter, H., J. Org. Chem., 1970, vol. 35, p. 295.

    Google Scholar 

  6. Ceccherelli, P., Curini, M., Epifano, F., Marcotullio, M.C., and Rosati, O., Synth. Commun., 1998, vol. 28, p. 3057.

    Google Scholar 

  7. Olah, G.A. and Gupta, B.C., Synthesis, 1980, p. 44.

  8. Arai, N. and Narasaka, K., Chem. Lett., 1995, p. 987.

  9. Ballini, R. and Petrini, M., Tetrahedron Lett., 1989, vol. 30, p. 5329.

    Google Scholar 

  10. Williams, J.R., Anger, L.G., and Moore, R.H., J. Org. Chem., 1978, vol. 43, p. 1271.

    Google Scholar 

  11. McMurry, J.E., Melton, J., and Padgett, H., J. Org. Chem., 1974, vol. 39, p. 259.

    Google Scholar 

  12. Bailey, A.J., Griffith, W.P., Mostafa, S., and Sherwood, P.A., Inorg. Chem., 1993, vol. 32, p. 268.

    Google Scholar 

  13. Zhao, C.-X., Acta Chim. Sinica, 1987, vol. 45, p. 83.

    Google Scholar 

  14. Bartlett, P.A., Green, F.R. III, and Webb, T.R., Tetrahedron Lett., 1977, p. 331.

  15. Adam, W., Mikosza, M., Saha-Miller, C.R., and Zhao, C.-G., Synlett, 1998, p. 1335.

  16. Kornblum, N. and Wade, P.A., J. Org. Chem., 1973, vol. 38, p. 1418.

    Google Scholar 

  17. Tokunaga, Y., Masataka, I., and Fukumoto, K., J. Chem. Soc., Perkin Trans., 1997, p. 207.

  18. Wawzonek, S. and Su, T.-Y., J. Electrochem. Soc., 1973, vol. 120, p. 745.

    Google Scholar 

  19. Nokami, J., Sonoda, T., and Wakabayashi, S., Synthesis, 1983, p. 763.

  20. Miyakoshi, T., Synthesis, 1986, p. 766.

  21. Patrick, H.W., Org. React., 1990, vol. 38, p. 665.

    Google Scholar 

  22. Bose, D.S. and Vanajatha, G., Synth. Comm., 1998, vol. 28, p. 4531.

    Google Scholar 

  23. Battersby, A.B., Baker, M.G., Broadbent, H.A., Fookes, C.J.R., and Leeper, F.J., J. Chem. Soc. Perkin Trans. 1, 1987, p. 2027.

  24. Chasar, D.W., Synthesis, 1982, p. 841.

  25. Ballini, R., Petrini, M., and Risini, G., Synthesis, 1987, p. 711.

  26. Fischer, R.H., Synthesis, 1980, p. 261.

  27. Fischer, R.H. and Weinz, H.M., Liebigs Ann. Chem., 1979, p. 612.

  28. Miyakoshi, T., J. Jpn. Oil Chemist's Soc. (Yukagaku), 1988, vol. 37, p. 19.

    Google Scholar 

  29. Koremura, M., Oku, H., Shono, T., and Nakanishi, T., Takamine Kenkyusho Nempo, 1961, vol. 13, p. 198.

    Google Scholar 

  30. Pirillo, D., Rescia, G., Traverso, G., and De Paoli, A., Farmaco Ed. Sci., 1980, vol. 35, p. 324.

    Google Scholar 

  31. Ogibin, Yu.N., Maksimova, N.G., Kondrashina, G.E., and Nikishin, G.I., Zh. Org. Khim., 1970, vol. 6, p. 1390.

    Google Scholar 

  32. Ogibin, Yu.N., Troyanskii, E.I., and Nikishin, G.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1974, p. 2239.

  33. Gilbert, B.C. and Norman, R.O.C., Can. J. Chem., 1982, vol. 60, p. 1379.

    Google Scholar 

  34. Kaplan, R.B. and Schechter, H., J. Am. Chem. Soc., 1961, vol. 83, p. 3535.

    Google Scholar 

  35. Matacz, Z., Piotrowska, H., and Urbanski, T., Pol. J. Chem., 1979, vol. 53, p. 187.

    Google Scholar 

  36. Kornblum, N., Singh, H.K., and Kelly, W.J., J. Org. Chem., 1983, vol. 48, p. 332.

    Google Scholar 

  37. Tselinskii, I.V., Mel'nikova, S.F., and Fedotov, S.A., Izv. Acad. Nauk, Ser. Khim., 2002, p. 1354.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. N. Ogibin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ogibin, Y.N., Ilovaiskii, A.I., Merkulova, V.M. et al. Electrolysis of Nitro Compound Salts: Application in Ketone Synthesis. Russian Journal of Electrochemistry 39, 1220–1227 (2003). https://doi.org/10.1023/B:RUEL.0000003449.72748.b2

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUEL.0000003449.72748.b2

Navigation