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Tautomerism and self-conversion of substituted 2-thiophenethiols. Substituent effects and self-thiylation mechanism

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The substitutent effect on the self-thiylation of 2-thiophenethiols was studied. Experimental results and quantum chemical calculations suggested possible mechanisms for this reaction dependent on the reaction conditions.

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References

  1. V. Yu. Vvedenskii, S. V. Zinchenko, T. A. Shkarupa, N. A. Korchevin, É. N. Deryagina, and M. G. Voronkov, Dokl. Akad. Nauk SSSR,305, 624 (1989).

    Google Scholar 

  2. G. S. Ponticello, C. N. Habecker, S. L. Varga, and S. M. Pitzenberger, J. Org. Chem.,54, 3223 (1989).

    Article  Google Scholar 

  3. M. V. Ul'yev, E. D. Shtefan, and V. Yu. Vvedenskii, Usp. Khim.,60, 2528 (1991).

    Google Scholar 

  4. E. D. Shtefan and V. Yu. Vvedenskii, Usp. Khim.,65, 326 (1996).

    Google Scholar 

  5. V. Yu. Vvedenskii, T. A. Shkarupa, S. V. Zinchenko A. R. Zhnikin, É. N. Deryagina, and M. G. Voronkov, Zh. Org. Khim.,26, 2237 (1990).

    Google Scholar 

  6. E. Jones and I. M. Moodie, Tetrahedron,21, 1333 (1965).

    Article  Google Scholar 

  7. S. Gronowitz (ed.), Thiophene and Its Derivatives, Part 3, Interscience Publ., New York (1986), Ch. 1, p. 40.

    Google Scholar 

  8. V. Yu. Vvedenskii, E. D. Shtefan, M. V. Ul'yev, A. R. Zhnikin, T. A. Shkarupa, É. N. Deryagina, and M. G. Voronkov, Zh. Org. Khim.,28, 212 (1992).

    Google Scholar 

  9. A. V. Anisimov, V. F. Ionova, and V. A. Viktorova, Khim. Geterotsikl. Soedin., No. 2, 186 (1978).

    Google Scholar 

  10. S. Gronowitz, P. Mozes, and A.-B. Hornfeldt, Ark. Kemi.,17, 237 (1961).

    Google Scholar 

  11. V. Yu. Vvedenskii [Vvedensky], E. D. Shtefan, M. V. Ul'yev [Ulyev], É. N. Deryagina [E. N. Deryagina], and M. G. Voronkov, Sulfur Lett.,17, 257 (1994).

    Google Scholar 

  12. V. Yu. Vvedenskii, E. D. Shtefan, R. N. Malyushenko, and É. N. Deryagina, Khim. Geterotsikl. Soedin., No. 7, 891 (1994).

    Google Scholar 

  13. Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1696 (1960).

    Google Scholar 

  14. S. Gronowitz and R. A. Hoffman, Ark. Kemi,15, 499 (1960).

    Google Scholar 

  15. Ya. L. Gol'dfarb and M. A. Kalik, Khim. Geterotsikl. Soedin. No. 5, 788 (1968).

    Google Scholar 

  16. S. T. Purcell, N. Garcia, V. T. Binh, L. Jones, and J. M. Tour, J. Am. Chem. Soc.,116, 11985 (1994).

    Article  Google Scholar 

  17. S. Ducher and A. Michet, Bull. Soc. Chim. France, No. 3 (Part 2), 1037 (1973).

    Google Scholar 

  18. E. N. Prilezhaeva and M. F. Shostakovskii, Usp. Khim.,32, 897 (1963).

    Google Scholar 

  19. S. Gronowitz, Khim. Geterotsikl. Soedin., Nos. 11/12, 1445 (1994).

    Google Scholar 

  20. V. Yu. Vvedenskii, S. V. Zinchenko, E. D. Shtefan, M. V. Ul'yev, A. R. Zhnikin, T. A. Shkarupa, and É. N. Deryagina, Dokl. Akad. Nauk SSSR,320, 96 (1991).

    Google Scholar 

  21. V. Yu. Vvedenskii [Vvedensky], S. V. Zinchenko, E. D. Shtefan, M. V. Ul'yev [Ulyev], A. R. Zhnikin, T. A. Shkarupa, and É. N. Deryagina [E. N. Deryagina], Sulfur Lett.,14, 129 (1992).

    Google Scholar 

  22. H. J. Jakobsen, E. N. Larsen, and S.-O. Lawesson, Tetrahedron,19, 1867 (1963).

    Article  Google Scholar 

  23. L. L. Gershbein and C. D. Hurd, J. Am. Chem. Soc.,69, 241 (1947).

    Article  Google Scholar 

  24. K. Ruhlmann, D. Heuchel, U. Schrapler, and D. Gramer, J. Prakt. Chem.,11, 40 (1960).

    Article  Google Scholar 

  25. J. M. Tour, L. R. Jones II, D. L. Pearson, J. J. S. Lamba, T. P. Burgin, G. M. Whitesides, D. L. Allara, A. N. Parikh, and S. V. Atre, J. Am. Chem. Soc.,117, 9529 (1995).

    Article  Google Scholar 

  26. A. V. Anisimov, E. A. Viktorova, and T. A. Danilova, Molecular Rearrangements of Organosulfur Compounds [in Russian], Izd. Moskovsk. Gos. Univ., Moscow (1989), p. 67.

    Google Scholar 

  27. V. Yu. Vvedenskii [Vvedensky], E. D. Shtefan, R. N. Malyushenko, and É. N. Deryagina [E. N. Deryagina], Sulfur Lett.,18(4), 173 (1995).

    Google Scholar 

  28. A. R. Katritzky, M. Szafran, and J. Stevens, J. Mol. Struct. (Theochem),184, 179 (1989).

    Article  Google Scholar 

  29. K. Tamao, S. Kodama, I. Nakajima, M. Kumada, A. Minato, and K. Suzuki, Tetrahedron,38, 3347 (1982).

    Google Scholar 

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Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of Russia, 664033 Irkutsk, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1203–1218, September, 1997.

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Vvedenskii, V.Y., Shtefan, E.D., Malyushenko, R.N. et al. Tautomerism and self-conversion of substituted 2-thiophenethiols. Substituent effects and self-thiylation mechanism. Chem Heterocycl Compd 33, 1047–1061 (1997). https://doi.org/10.1007/BF02253219

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  • DOI: https://doi.org/10.1007/BF02253219

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