Skip to main content
Log in

Electrochemical oxidation of 1,1-dihydroxy-4-methylcyclohexane on platinum anode. Synthesis of 3,12-dimethyl-7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecane

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

Abstract

The possibility is shown of electrochemical synthesis of 3,12-dimethyl-7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecane that belong to the class of 1,2,4,5-tetraoxanes by oxidation of 1,1-dihydroperoxy-4-methylcyclohexane using a Pt anode.

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.

References

  1. Jefford, C.W., Adv. Drug Res., 1997, vol. 29, p. 271.

    Article  CAS  Google Scholar 

  2. O’Neil, P.M. and Posner, G.H., J. Med. Chem., 2004, vol. 47, p. 2945.

    Article  Google Scholar 

  3. Dong, Y., Mini-Rev. Med. Chem., 2002, vol. 2, p. 113.

    Article  CAS  Google Scholar 

  4. Vennerstrom, J.L., Fu, H.-N., Ellis, W.Y., Ager, A.L., Wood, J.K., Andersen, S.L., Gerena, L., and Milhous, W.K., J. Med. Chem., 1992, vol. 35, p. 3023.

    Article  CAS  Google Scholar 

  5. Gelb, M.H., Curr. Opin. Chem. Biol., 2007, vol. 11, p. 440.

    Article  CAS  Google Scholar 

  6. Najjar, F., Gorrichon, L., Baltas, M., André-Barrès, C., and Vial, H., Org. Biomol. Chem., 2005, vol. 3, p. 1612.

    Article  CAS  Google Scholar 

  7. Ellis, G.L., Amewu, R., Hall, C., Rimmer, K., Ward, S.A., and O’Neill, P.M., Bioorg. Med. Chem., 2008, vol. 18, p. 1720.

    Article  CAS  Google Scholar 

  8. Hamada, Y., Tokuhara, H., Masuyama, A., Nojima, M., Kim, H.-S., Ono, K., Ogura, N., and Wataya, Y., J. Med. Chem., 2002, vol. 45, p. 1374.

    Article  CAS  Google Scholar 

  9. Dembitsky, V.M., Eur. J. Med. Chem., 2008, vol. 43, p. 223.

    Article  CAS  Google Scholar 

  10. Terzić, N., Opsenica, D., Mili, D., Tinant, B., Smith, K.S., and Milhous, W.K., J. Med. Chem., 2007, vol. 50, p. 5118.

    Article  Google Scholar 

  11. Amewu, R., Stachulski, A.V., Ward, S.A., Berry, N.G., Bray, P.G., Davies, J., Labat, G., Vivas, L., and O’Neill, P.M., Org. Biomol. Chem., 2006, vol. 4, p. 4431.

    Article  CAS  Google Scholar 

  12. Dong, Y., Tang, Y., Chollet, J., Matile, H., Wittlin, S., Charman, S.A., Charman, W.N., Tomas, J.S., Scheurer, C., Snyder, C., Scorneaux, B., Bajpai, S., Alexander, S.A., Wang, X., Padmanilayam, M., Cheruku, S.R., Brun, R., and Vennerstrom, J.L., Bioorg. Med. Chem., 2006, vol. 14, p. 6368.

    Article  CAS  Google Scholar 

  13. Singh, C., Malik, H., and Puri, S.K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 459.

    Article  CAS  Google Scholar 

  14. De Vries, B., Van Swieten, A.P., Syed, E.A., and Akzo Nobel, N.V., Neth., WO no. 2003070699.

  15. Davis, O.L., Dorn, O., Dorn, R.W., and Calif, P.H., Shell Oil Co., US no. 3151170.

  16. Sacharova, A.A., Vygodsky, Ya.S., Terent’ev, A.O., Platonov, M.M., Sapozhnikov, D.A., Volkova, T.V., and Nikishin, G.I., Application RU, 25.12.2007, no. 2007147786.

  17. Terent’ev, A.O., Sacharova, A.A., Vygodsky, Ya.S., Platonov, M.M., Sapozhnikov, D.A., Volkova, T.V., and Nikishin, G.I., Application RU, 01.04.2008, no. 2008112023.

  18. Terent’ev, A.O., Platonov, M.M., Kashin, A.S., and Nikishin, G.I., Tetrahedron, 2008, vol. 64, p. 7944.

    Article  Google Scholar 

  19. Terent’ev, A.O., Platonov, M.M., Ogibin, Yu.N., and Nikishin, G.I., Synth. Commun., 2007, vol. 37, p. 1281.

    Article  Google Scholar 

  20. Terent’ev, A.O., Kutkin, A.V., Platonov, M.M., Ogibin, Yu.N., and Nikishin, G.I., Tetrahedron Lett., 2003, vol. 44, p. 7359.

    Article  Google Scholar 

  21. Žmitek, K., Zupan, M., Stavber, S., and Iskra, J., J. Org. Chem., 2007, vol. 72, p. 6534.

    Article  Google Scholar 

  22. Žmitek, K., Zupan, M., Stavber, S., and Iskra, J., Org. Lett., 2006, vol. 8, p. 2491.

    Article  Google Scholar 

  23. Horozova, E., Dimcheva, N., and Jordanova, Z., Bioelectrochemistry, 2002, vol. 58, p. 181.

    Article  CAS  Google Scholar 

  24. Laine Derek, F., Roske Christopher, W., Cheng, I. Francis, Anal. Chim. Acta, 2008, vol. 608, p. 56.

    Article  CAS  Google Scholar 

  25. Begum, Nadira Ferdousi, Md., Mominul Islam, Takeyoshi Okajima, and Takeo Ohsaka, Electrochim. Acta, 2007, vol. 53, p. 968.

    Article  Google Scholar 

  26. Baron, R., Darchen, A., and Hauchard, D., Electrochim. Acta, 2006, vol. 51, p. 1336.

    Article  CAS  Google Scholar 

  27. Najjar, F., Andres-Barres, C., Baltas, M., Lacaze-Dufaure, C., Magri, D.C., Workentin, M.S., and Tzedakis, T., Chem.-Eur. J., 2007, vol. 13, p. 1174.

    Article  CAS  Google Scholar 

  28. Najjar, F., Baltas, M., Gorrichon, L., Moreno, Y., Tzedakis, T., Vial, H., and Andres-Barres, C., Eur. J. Org. Chem., 2003, p. 335.

  29. Dong, Y. and Vennerstrom, J., J. Org. Chem., 1998, vol. 63, p. 8582.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. D. Vedenyapina.

Additional information

Original Russian Text © M.D. Vedenyapina, A.O. Terent’ev, M.M. Platonov, A.M. Skundin, A.A. Vedenyapin, G.I. Nikishin, 2011, published in Elektrokhimiya, 2011, Vol. 47, No. 2, pp. 251–254.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vedenyapina, M.D., Terent’ev, A.O., Platonov, M.M. et al. Electrochemical oxidation of 1,1-dihydroxy-4-methylcyclohexane on platinum anode. Synthesis of 3,12-dimethyl-7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecane. Russ J Electrochem 47, 234–237 (2011). https://doi.org/10.1134/S102319351012102X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S102319351012102X

Keywords

Navigation