Log in

Reaction of unsaturated compounds with ethyl benzenesulfenate and trimethylsilyl isothiocyanate

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new method for the synthesis of thiocyanato- and isothiocyanatoalkyl phenyl sulfides by the reaction of unsaturated compounds with ethyl benzenesulfenate and trimethylsilyl isothiocyanate has been suggested. Regio- and stereoselectivity of the reaction was studied, having taken alkenes, dienes, and alkynes as examples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. N. V. Zyk, A. Yu. Gavrilova, O. A. Mukhina, O. B. Bondarenko, N. S. Zefirov, Izv. Akad. Nauk, Ser. Khim., 2008, 2521 [Russ. Chem. Bull., Int. Ed., 2008, 57, 2572].

    Google Scholar 

  2. N. Kharasch, H. L. Wehrmeister, H. Tigerman, J. Am. Chem. Soc., 1947, 60, 1612.

    Article  Google Scholar 

  3. I. V. Bodrikov, L. I. Kovaleva, L. V. Chumakov, N. S. Zefirov, Zh. Org. Khim., 1978, 14, 2457 [J. Org. Chem. USSR (Engl. Transl.), 1978, 14].

    CAS  Google Scholar 

  4. A. K. Mukerjee, R. Ashare, Chem. Rev., 1991, 91, 1.

    Article  CAS  Google Scholar 

  5. G. H. Posner, Ch.-G. Cho, J. V. Green, J. Med. Chem., 1994, 37, 170.

    Article  CAS  Google Scholar 

  6. E. Elhalem, B. N. Bailey, R. Docampo, I. Ujváry, S. H. Szajnman, J. B. Rodriguez, J. Med. Chem., 2002, 45, 3984.

    Article  CAS  Google Scholar 

  7. T. Marsman, Chem. Zeitung, 1972, 96, 288.

    Google Scholar 

  8. E. V. Van Der Berghe, G. P. Van Der Kelen, J. Organomet. Chem., 1974, 82, 345.

    Article  Google Scholar 

  9. M. Witanowski, L. Stefaniak, G. A. Webb, in Annual Reports on NMR Spectroscopy, 7, Ed. G. A. Webb, Academic Press, London, 1977, 117.

    Google Scholar 

  10. L. J. Bellamy, The Infra-Red Spectra of Complex Molecules, J. Wiley and Sons, New-York, 1957.

    Google Scholar 

  11. G. C. Levy, G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, J. Wiley and Sons, Chichester—New York—London—Sydney—Toronto, 1972.

    Google Scholar 

  12. D. G. Garrat, Can. J. Chem., 1979, 57, 2180.

    Article  Google Scholar 

  13. A. J. Gordon, R. A. Ford, The Chemist’s companion, A Wiley-Interscience publication, John Wiley and Sons, New York—London—Sydney—Toronto, 1972.

    Google Scholar 

  14. N. S. Zefirov, I. V. Bodrikov, Zh. Org. Khim., 1983, 19, 2225 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  15. A. O. Chizhov, N. S. Zefirov, N. V. Zyk, T. C. Morrill, J. Org. Chem., 1987, 52, 5647.

    Article  CAS  Google Scholar 

  16. H. Gunter, NMR Spectroscopy. An Introduction, J. Wiley and Sons, Chichester—New York—Brisbane—Toronto, 1980.

    Google Scholar 

  17. I. V. Koval’, Usp. Khim., 1995, 64, 781 [Russ. Chem. Rev. (Engl. Transl.), 1995, 64].

    Google Scholar 

  18. G. H. Schmid, V. M. Csizmadia, V. J. Nowlan, D. G. Garratt, Can. J. Chem., 1972, 50, 2457.

    Article  CAS  Google Scholar 

  19. G. H. Schmid, D. G. Garratt, Tetrahedron, 1978, 34, 2869.

    Article  CAS  Google Scholar 

  20. B. M. Trost, S. D. Ziman, J. Org. Chem., 1973, 38, 932.

    Article  CAS  Google Scholar 

  21. D. G. Garratt, M. D. Ryan, M. Ujjainwalla, Can. J. Chem., 1979, 57, 2145.

    Article  CAS  Google Scholar 

  22. F. G. Cocu, G. Wolczunowicz, L. Bors, Th. Posternak, Helv. Chim. Acta, 1970, 53, 739.

    Article  CAS  Google Scholar 

  23. K. Hartke, H.-U. Gleim, Liebigs Ann. Chem., 1976, 716.

  24. E. K. Beloglazkina, M. A. Belova, R. L. Antipin, N. V. Zyk, A. K. Buryak, Zh. Org. Khim., 2003, 39, 549 [Russ. J. Org. Chem. (Engl. Transl.), 2003, 39].

    Google Scholar 

  25. H. Gunter, G. Jikeli, Chem. Rev., 1977, 77, 599.

    Article  Google Scholar 

  26. O. Korver, T. L. Kwa, C. Boelhouwer, Tetrahedron, 1968, 24, 1025.

    Article  CAS  Google Scholar 

  27. N. V. Zyk, E. K. Beloglazkina, M. A. Belova, N. S. Zefirov, Izv. Akad. Nauk, Ser. Khim., 2000, 1874 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1846].

    Google Scholar 

  28. N. V. Zyk, E. K. Beloglazkina, M. A. Belova, S. V. Zatonsky, N. S. Zefirov, Phosphorus, Sulfur, Silicon, Relat. Elem., 2002, 177, 555.

    Article  CAS  Google Scholar 

  29. G. H. Schmid, A. Modro, F. Lenz, D. G. Garratt, K. Yates, J. Org. Chem., 1976, 41, 2331.

    Article  CAS  Google Scholar 

  30. L. Chang, D. B. Denney, D. Z. Denney, K. J. Kazior, J. Am. Chem. Soc., 1977, 99, 2293.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Gavrilova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1724–1733, September, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zyk, N.V., Gavrilova, A.Y., Mukhina, O.A. et al. Reaction of unsaturated compounds with ethyl benzenesulfenate and trimethylsilyl isothiocyanate. Russ Chem Bull 59, 1771–1780 (2010). https://doi.org/10.1007/s11172-010-0311-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0311-0

Key words

Navigation