Skip to main content
Log in

The production of episulfonium complexes from propylene and the regioselectivity of their reactions with nucleophiles

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The regioselectivity of the reactions of stable S-arylsulfonium complexes prepared from propylene and various nucleophiles corresponds to Markovnikov addition and the degree of selectivity of this reaction depends on the nature of the aromatic substituent. The episulfonium complexes prepared were characterized by13C NMR spectra.

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

Literature cited

  1. E. A. Vorob'eva, M. Z. Krimer, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 125 (1975).

  2. P. Reynolds, S. Zonnebelt, S. Bakker, and M. Kellogg, J. Am. Chem. Soc.,96, 3146 (1974).

    Google Scholar 

  3. G. H. Schmid and D. G. Garratt, Tetrahedron Lett., 3991 (1975).

  4. M. Oki, W. Nakanishi, M. Fukunaga, G. D. Smith, W. Duak, and Y. Osava, Chem. Lett., 1277 (1975).

  5. W. H. Mueller and P. E. Butler, J. Am. Chem. Soc.,90, 2075 (1968).

    Google Scholar 

  6. L. M. Jackman, Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed., Pergamon Press, New York (1969).

    Google Scholar 

  7. G. Schmid and D. Garratt, Can. J. Chem.,15, 2463 (1973).

    Google Scholar 

  8. W. H. Mueller, Angew. Chem. Int. Ed.,8, 482 (1969).

    Google Scholar 

  9. D. Owsley, G. Helmkamp, and M. Pettit, J. Am. Chem. Soc.,91, 5239 (1969).

    Google Scholar 

  10. D. Garratt and G. Schmid, Can. J. Chem.,52, 1027 (1974).

    Google Scholar 

  11. É. A. Vorob'eva, M. Z. Krimer, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 2743 (1976).

  12. É. A. Vorob'eva, M. Z. Krimer, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 1318 (1976).

  13. N. S. Zefirov, N. K. Sadovaya (Sadovaja), A. M. Mageratov, and J. V. Bodrikov, Tetrahedron,31, 2948 (1975).

    Google Scholar 

  14. V. R. Kartashev, J. Bodrikov, E. A. Skorobogatova, and N. S. Zefirov, Int. J. Sulfur Chem.,3, 213 (1977).

    Google Scholar 

  15. N. Kharash, C. Buess, and S. Strashum, J. Am. Chem. Soc.,74, 3422 (1952).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 563–572, March, 1979.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gybin, A.S., Krimer, M.Z., Smit, V.A. et al. The production of episulfonium complexes from propylene and the regioselectivity of their reactions with nucleophiles. Russ Chem Bull 28, 518–526 (1979). https://doi.org/10.1007/BF00924824

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00924824

Keywords

Navigation