Skip to main content
Log in

Oxidation of polyfunctional sulfides with chlorine dioxide

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

3-Benzylsulfanyl-4,5-diphenyl-4H-1,2,4-triazole, 5-methylsulfanyl-1-phenyl-1H-tetrazole, 2-methylsulfanyl-1H-benzimidazole, 2-benzylsulfanyl-1H-benzimidazole, and 1-butylsulfanyl-4-nitrobenzene were oxidized to the corresponding sulfoxides with chlorine dioxide using different modes of oxidant supply. The oxidation process was characterized by high chemoselectivity.

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. Minoru, U., Chem. Pharm. Bull., 1989, vol. 37, p. 210.

    Google Scholar 

  2. Holt, S. and Howden, C.W., Dig. Dis. Sci., 1991, vol. 36, p. 385.

    Article  CAS  Google Scholar 

  3. Shin, J.M., Cho, Y.M., and Sachs, G., J. Am. Chem. Soc., 2004, vol. 126, p. 7800.

    Article  CAS  Google Scholar 

  4. Kowalski, P., Mitka, K., Ossowska, K., and Kolarska, Z., Tetrahedron, 2005, vol. 61, p. 1933.

    Article  CAS  Google Scholar 

  5. Fernandez, I. and Khiar, N., Chem. Rev., 2003, vol. 103, p. 3651.

    Article  CAS  Google Scholar 

  6. Graber, D.R., Morge, R.A., and Sih, J.C., J. Org. Chem., 1987, vol. 52, p. 4620.

    Article  CAS  Google Scholar 

  7. Masakazu, I. and Yasuhiro, T., Catal. Surv. Jpn., 2001, vol. 1, p. 25.

    Google Scholar 

  8. Matsugi, M., Fukuda, N., Minamikawa, J.-i., and Otsuka, S., Tetrahedron Lett., 1998, vol. 39, p. 5591.

    Article  CAS  Google Scholar 

  9. Xu, L., Cheng, J., and Trudell, M.L., J. Org. Chem., 2003, vol. 68, p. 5388.

    Article  CAS  Google Scholar 

  10. Blaser, H.U., Spindler, F., and Studer, M., Appl. Catal. A: General, 2001, vol. 221, p. 119.

    Article  CAS  Google Scholar 

  11. Okabe, S., Satoh, M., Yamakawa, T., Nomura, Y., and Hayashi, M., UK Patent Appl. no. 2 163 747, 1986.

  12. Gol’tsberg, M.A. and Koldobskii, G.I., Russ. J. Org. Chem., 1996, vol. 32, p. 1194.

    Google Scholar 

  13. Egorov, N.E., Artamonova, T.V., and Koldobskii, G.I., Russ. J. Org. Chem., 2007, vol. 42, p. 475.

    Article  Google Scholar 

  14. Hrabalek, A., Myznikov, L., Kunes, J., Vavrova, K., and Koldobskii, G., Tetrahedron Lett., 2004, vol. 45, p. 7955.

    Article  CAS  Google Scholar 

  15. Galliani, G. and Rindone, B., J. Chem. Res., Synop., 1981, p. 74.

  16. Kuchin, A.V., Rubtsova, S.A., Loginova, I.V., and Subbotina, S.N., Russ. J. Org. Chem., 2000, vol. 36, p. 1819.

    CAS  Google Scholar 

  17. Kuchin, A.V., Rubtsova, S.A., and Loginova, I.V., Izv. Ross. Akad. Nauk, Ser. Khim., 2001, p. 813.

  18. Loginova, I.V., Ashikhmina, E.V., Rubtsova, S.A., Krymskaya, Yu.V., and Kuchin, A.V., Russ. J. Org. Chem., 2008, vol. 44, p. 1773.

    Article  CAS  Google Scholar 

  19. Loginova, I.V., Rubtsova, S.A., and Kuchin, A.V., Khim. Prirodn. Soedin., 2008, no. 6, p. 608.

  20. Karaulova, E.N., Sintez sul’fidov, tiofenov i tiolov tipa soedinenii, vstrechayushchikhsya v neftyakh (Synthesis of Sulfides, Thiophenes, and Thiols Like Compounds Occurring in Oils), Moscow: Nauka, 1988, p. 208.

    Google Scholar 

  21. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  Google Scholar 

  22. Muhi-Eldeen, Z., Nadir, M., Aljobory, N.R., Husseen, F., and Stohs, S.J., Eur. J. Med. Chem., 1991, vol. 26, p. 237.

    Article  CAS  Google Scholar 

  23. Lakouraj, M.M., Tajbakhsh, M., Shirini, F., Asady Tamami, M.V., Synth. Commun., 2005, vol. 35, no. 6, p. 775.

    Article  CAS  Google Scholar 

  24. Jiang, B., Zhao, X.-L., Dong, J.-J., and Wang, W.-J., Eur. J. Org. Chem., 2009, p. 987.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. V. Loginova.

Additional information

Original Russian Text © I.V. Loginova, K.S. Rodygin, S.A. Rubtsova, P.A. Slepukhin, A.V. Kuchin, V.A. Polukeev, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 125–130.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Loginova, I.V., Rodygin, K.S., Rubtsova, S.A. et al. Oxidation of polyfunctional sulfides with chlorine dioxide. Russ J Org Chem 47, 124–130 (2011). https://doi.org/10.1134/S1070428011010167

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011010167

Keywords

Navigation