Skip to main content
Log in

Interaction of dimethylsulfoxonium methylide with 5-allyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Dimethylsulfoxonium methylide in DMSO initiates unusual oxidative skeletal transformations of trichlorocyclopentenone. Lactone, cyclic orthoester, and a number of by-products of hydrolysis, substitution, and reduction were isolated and characterized. The expected epoxide was obtained in low yield.

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. E. J. Corey and M. Chaykovsky,J. Am. Chem. Soc., 1965,87, 1353.

    Google Scholar 

  2. R. J. Carlson and N. S. Behn,J. Org. Chem., 1967,32, 1363.

    Google Scholar 

  3. C. R. Johnson and G. F. Katekar,J. Am. Chem. Soc., 1970,92, 5751

    Google Scholar 

  4. D. C. Clark and D. J. Goldsmith,Org. Prep. Proceed. Int., 1972,4, 113.

    Google Scholar 

  5. C. Agami and J. Aubonet,Bull Soc. Chim. Fr., 1967,5, 1391.

    Google Scholar 

  6. S. R, Landor and N, Punia,J. Chem. Soc., C, 1967, 2495.

  7. R. Faragher, T. L. Jilchrist, and I. M. Southon,Tetrahedron Lett., 1979,28, 4113; 4117.

    Google Scholar 

  8. N. B. Beeley and J. K. Sutherlaud,J. Chem. Soc., Chem. Commun., 1977, 321.

  9. A. Yurchenko, A. V. Kirii, I. R. Likhotvorik, N. N. Mel'nik, and A. O. Kushko,Ukr. Khim. Zh., 1992,58, 1106 (in Russian).

    Google Scholar 

  10. V. Tamara, T. Miyamoto, J.Eiho, H. Taniguchi, T. Nishimura, and V. Kita,J. Chem. Soc., Perkin Trans. I, 1974, 102; 105.

  11. V. Tamara, T. Miyamoto, T. Nishimura, and V. Kita,Tetrahedron Lett., 1973, 2351.

  12. B. M. Trost and L. S. Melvin, Jr.,Sulfur Ylides, Academic Press, New York, 1975.

    Google Scholar 

  13. S. A. Ismailov,Zh. Org. Khim., 1989,25, 2238 [J. Org. Chem. USSR, 1989,25 (Engl. Trans].)].

    Google Scholar 

  14. G. A. Tolstikov, S. A. Ismailov, Ya. L. Vel'der, and M. S. Miftakhov,Zh. Org. Khim., 1991,27, 83 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  15. G. A. Tolstikov, S. A. Ismailov, L. M. Khalilov, M. S. Miftakhov,Zh. Org. Khim., 1992,28, 438 [Russ. J. Org. Chem., 1992,28 (Engl. Transl.)].

    Google Scholar 

  16. M. S. Miftakhov, R. M. Khalikov, A. A. Fatykhov, and R. R. Akhmetvaleev,Izv. Akad. Nauk, Ser. Khim., 1995, 1169 [Russ. Chem. Bull., 1995,44, 1129 (Engl. Transl.)].

    Google Scholar 

  17. S. A. Ismailov, M. S. Miftakhov, and G. A. Tolstikov,Mendeleev Commun., 1991, 149.

  18. G. A. Tolstikov, R. M. Khalikov, S. A. Ismailov, R. R. Akhmetvaleev, and M. S. Miftakhov,Zh. Org. Khim., 1993,29, 342 [Russ. J. Org. Chem., 1993,29 (Engl. Transt.)].

    Google Scholar 

  19. M. S. Miftakhov, R. M. Khalikov, R. R. Akhmetvaleev, and G. A. Tolstikov,Zh. Org. Khim., 1995,31, 207 [Russ. J. Org. Chem., 1995,31 (Engl. Transl.)].

    Google Scholar 

  20. G. A. Tolstikov, S. A. Ismailov, Z. B. Badretdinova, G. G. Balezina, and M. S. Miftakhov,Zh. Org. Khim., 1991,27, 1878 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

  21. G. A. Tolstikov, S. A. Ismailov, Ya. V. Vel'der, and M. S. Miftakhov,Zh. Org. Khim., 1991,27, 90 [J. Org. Chem. USSR, 1991,27 (Engl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2958–2960, December, 1996.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivanova, N.A., Shainurova, A.M., Furlei, I.I. et al. Interaction of dimethylsulfoxonium methylide with 5-allyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one. Russ Chem Bull 45, 2810–2812 (1996). https://doi.org/10.1007/BF01430648

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01430648

Key words

Navigation