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A study of the reactions of sulfur with organic compounds

XV. The action of sulfur on exo-halogen derivatives of ethylbenzene and styrene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

On the basis of the reaction of sulfur with exo-halogen derivatives of ethylbenzene and styrene, new and simple methods of synthesis have been developed for 2,4-diphenylthiophene (from C6H5CHBrCH3), 2, 5-diphenylthiophene (from C6H5CCl=CH2), 2,3-dichlorothionaphthene (from C6H5CCl2CHCl2), and the previously unknown dithianaphtheno-[2,3-b;2′,3′-e]-1,4-dithiadiene (from C6H5CHClCHClBr). The latter compound is also formed by the action of sulfur on C6H5CCl2CH2Cl or C6H5CHClCHCl2 in the presence of HBr. The derivatives of thianaphthene obtained have been oxidized to the corresponding sulfones.

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References

  1. M. G. Voronkov, A. N. Pereferkovich, V. A. Pestunovich, and V. E. Udre, ZhOrKh, 3, 2211, 1967.

    Google Scholar 

  2. M. G. Voronkov and V. E. Udre, KhGS [Chemistry of Heterocyclic Compounds], 148, 683, 1965.

    Google Scholar 

  3. M. G. Voronkov and V. E. Udre, KhGS [Chemistry of Heterocyclic Compounds], 527, 1966.

  4. E. Baumann and E. Fromm, Ber., 28, 890, 895, 1895.

    Google Scholar 

  5. E. Baumann and E. Fromm, Ber., 30, 110, 1897.

    Google Scholar 

  6. K. Meyer and W. Hohenemser, Helv. Chim. Acta, 18, 1061, 1935.

    Google Scholar 

  7. H. Westeche, Chem. Rev., 39, 219, 1946.

    Google Scholar 

  8. L. Drake, US Patent 2538722, 1951; C. A., 45, 4269, 1951.

    Google Scholar 

  9. H. Glass and E. Reid, J. Am. Chem. Soc, 51, 3428, 1929.

    Google Scholar 

  10. M. G. Voronkov and V. E. Udre, Authors' Certificate 1050577/23-4, 1966.

  11. A. Schlesinger and D. Mowry, J. Am. Chem. Soc, 73, 2614, 1931.

    Google Scholar 

  12. O. Johnson, A. Harvey, and H. West, U. S. Patent 2758955, 1956; C. A., 50, 6027, 1956.

    Google Scholar 

  13. D. Cagniant, P. Faller, and P. Cagniant, Bull. Soc chim. France, 2410, 1961.

  14. A. Dinesmann, C. r., 141, 201, 1905.

    Google Scholar 

  15. G. Barger, J. Chem. Soc, 95, 2194, 1909.

    Google Scholar 

  16. O. Kamm and C. Marvel, Org. Synt., 1, 23, 1937.

    Google Scholar 

  17. H. Biltz, Ann., 296, 263, 1897.

    Google Scholar 

  18. C. Glaser, Ann., 154, 155, 1870.

    Google Scholar 

  19. E. Erlenmeyer, Ber., 13, 306, 1880.

    Google Scholar 

  20. K. Auwers, Ber., 45, 2799, 1912.

    Google Scholar 

  21. E. Fromm, P. Fantl, and E. Leibsohn, Ann., 457, 275, 1937.

    Google Scholar 

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For communication XIV see [1].

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Voronkov, M.G., Udre, V.E. & Popova, E.P. A study of the reactions of sulfur with organic compounds. Chem Heterocycl Compd 3, 784–788 (1967). https://doi.org/10.1007/BF00474868

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  • DOI: https://doi.org/10.1007/BF00474868

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