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Synthesis of β-trifluoroacetyl-substituted vinyl sulfones and vinyl sulfides

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Abstract

Oxidation of β-(trifluoroacetyl)vinyl sulfides afforded a series of the corresponding sulfones. The reactions of sulfones with various alkyl- and arylthiols were studied. These reactions provide the basis for a new procedure for the synthesis of β-(trifluoroacetyl)vinyl sulfides.

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References

  1. R. V. C. Carr and L. A. Paquette, J. Am. Chem. Soc., 1980, 102, 853.

    Google Scholar 

  2. N. S. Simpkins, Tetrahedron, 1990, 46, 6951; O. De Lucchi and L. Pasquato, Tetrahedron, 1988, 44, 6755.

    Google Scholar 

  3. B. M. Trost, H. C. Arndt, P. E. Strege, and T. R. Verhoeven, Tetrahedron Lett., 1976, 3477.

  4. L. A. Paquette, R. V. C. Carr, M. C. Boehm, and R. Gleiter, J. Am. Chem. Soc., 1980, 102, 1186.

    Google Scholar 

  5. L. A. Paquette and R. V. C. Carr, J. Am. Chem. Soc., 1980, 102, 7553.

    Google Scholar 

  6. O. De Lucchi and L. Pasquato, Gazz. Chim. Ital., 1984, 114, 349.

    Google Scholar 

  7. L. A. Paquette and R. V. Williams, Tetrahedron Lett., 1981, 22, 4643.

    Google Scholar 

  8. R. V. C. Carr, R. V. Williams, and L. A. Paquette, J. Org. Chem., 1983, 48, 4976.

    Google Scholar 

  9. O. De Lucchi, V. Lucchini, L. Pasquato, and G. Modena, J. Org. Chem., 1984, 49, 596.

    Google Scholar 

  10. U. Azzena, S. Cossu, O. De Lucchi, and G. Melloni, Tetrahedron Lett., 1989, 30, 1845.

    Google Scholar 

  11. N. Ono, A. Kamimura, and A. Kaji, Tetrahedron Lett., 1986, 27, 1595.

    Google Scholar 

  12. N. Ono, A. Kamimura, and A. Kaji, J. Org. Chem., 1988, 53, 251.

    Google Scholar 

  13. H. Kenji, Y. Mitsuaki, O. Satoru, and K. Ken, J. Am. Chem. Soc., 1984, 106, 6735.

    Google Scholar 

  14. T. A. Bryson, R. E. Dardis, and R. B. Gammill, Tetrahedron Lett., 1978, 8, 743.

    Google Scholar 

  15. H. N. Unn and S. Lars, J. Chem. Soc., Perkin Trans. 1, 1999, 21, 3085.

    Google Scholar 

  16. V. G. Nenajdenko and E. S. Balenkova, Tetrahedron., 1994, 50, 12407.

    Google Scholar 

  17. M. Hojo, R. Masuda, and Y. Kamitori, Tetrahedron Lett., 1976, 13, 1009.

    Google Scholar 

  18. N. P. Petukhova, N. E. Dontsova, O. M. Sazonova, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 2654 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978, 27, 2376 (Engl. Transl.)].

    Google Scholar 

  19. N. P. Petukhova, N. E. Dontsova, and E. N. Prilezhaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 2327 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982, 31 (Engl. Transl.)].

    Google Scholar 

  20. C. G. Venier, T. G. Squires, and Y. J. Chen, J. Org. Chem., 1982, 47, 3773.

    Google Scholar 

  21. V. G. Nenaidenko, A. V. Sanin, A. V. Churakov, J. A. K. Howard, and E. S. Balenkova, Khim. Geterotsikl. Soedin., 1999, 618 [Chem. Heterocycl. Compd., 1999 (Engl. Transl.)].

  22. A. L. Krasovsky, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2001, 57, 201.

    Google Scholar 

  23. V. G. Nenajdenko, A. L. Krasovsky, M. L. Lebedev, and E. S. Balenkova, Synlett, 1997, 12, 1349.

    Google Scholar 

  24. A. L. Krasovskii, V. G. Nenaidenko, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2001, 1329 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1395].

    Google Scholar 

  25. K. M. Gough and J. Millington, Can. J. Chem., 1995, 73, 1287.

    Google Scholar 

  26. T. Moriguchi, T. Endo, and T. Takata, J. Org. Chem., 1995, 60, 3523.

    Google Scholar 

  27. M. Hojo, R. Masuda, Y. Kamitori, and E. Okada, J. Org. Chem., 1991, 56, 1975.

    Google Scholar 

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Krasovsky, A.L., Nenajdenko, V.G. & Balenkova, E.S. Synthesis of β-trifluoroacetyl-substituted vinyl sulfones and vinyl sulfides. Russian Chemical Bulletin 51, 2080–2085 (2002). https://doi.org/10.1023/A:1021620228529

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  • DOI: https://doi.org/10.1023/A:1021620228529

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