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Thio-claisen rearrangement in the synthesis of sulfur-containing heterocyclic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The review is devoted to literature information on the mechanism of the thio-Claisen rearrangement of allyl aryl (heteryl) sulfides and their use in the synthesis of five- and six-membered sulfur-containing heterocyclic compounds, including derivatives of dihydrobenzothiophene and thiochromane.

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Literature cited

  1. R. B. Woodward and R. Hoffman, Angew. Chem., Int. Ed.,8, 781 (1969).

    Google Scholar 

  2. H. J. Hansen and H. Schmid, Chem. Brit., No. 2, 111 (1969).

    Google Scholar 

  3. L. Claisen, Ber.,45, 3757 (1912).

    Google Scholar 

  4. E. N. Karaulova, D. Sh. Meilanova, and G. D. Gal'pern, Dokl. Akad. Nauk SSSR,113, 1280 (1957).

    Google Scholar 

  5. E. N. Karaulova, D. Sh. Meilanova, and G. D. Gal'pern, Zh. Obshch. Khim.,27, 3034 (1957).

    Google Scholar 

  6. H. Kwart and N. A. Johnson, J. Am. Chem. Soc.,99, 3441 (1977).

    Google Scholar 

  7. H. Kwart and J. L. Schwartz, J. Org. Chem.,39, 1575 (1974).

    Google Scholar 

  8. S. J. Rhoads and N. R. Raulins, Org. Reactions,22, 1 (1975).

    Google Scholar 

  9. J. B. Bennet, Synthesis, No. 9, 589 (1977).

    Google Scholar 

  10. A. N. Korepanov, T. A. Danilova, and E. A. Viktorova, Neftekhimiya,16, 909 (1976).

    Google Scholar 

  11. É. A. Karakhanov, M. V. Vagabov, E. A. Viktorova, and A. Sh. Ramazanov, Vestn. Mosk. Univ., Ser. 2, Khim.,19, 362 (1978).

    Google Scholar 

  12. A. V. Anisimov, L. M. Kedik, L. P. Ermolenko, and E. A. Viktorova, Neftekhimiya,17, 148 (1977).

    Google Scholar 

  13. S. Oae, Organic Chemistry of Sulfur, Plenum, New York (1977).

    Google Scholar 

  14. J. C. Petropoulos, M. A. McCall, and D. S. Tarbell, J. Am. Chem. Soc.,75, 1130 (1953).

    Google Scholar 

  15. H. Kwart and M. H. Cohen, J. Org. Chem.,32, 3135 (1967).

    Google Scholar 

  16. H. Kwart and C. M. Hacket, J. Am. Chem. Soc.,84, 1754 (1962).

    Google Scholar 

  17. J. Meyers, C. Rinaldi, and J. Banoli, J. Org. Chem.,28, 2440 (1963).

    Google Scholar 

  18. H. Kwart and E. R. Evans, J. Org. Chem.,31, 413 (1966).

    Google Scholar 

  19. A. V. Anisimov, V. F. Ionova, and E. A. Viktorova, Zh. Org. Khim.,13, 2624 (1977).

    Google Scholar 

  20. H. Plieninger, H.-P. Kraemer, and H. Sirowej, Chem. Ber.,107, 3915 (1974).

    Google Scholar 

  21. J. Z. Mortensen, B. Hedegaard, and S.-O. Lawesson, Tetrahedron,27, 3832 (1971).

    Google Scholar 

  22. B. W. Bicroft and W. Landon, Chem. Commun., No. 3, 168 (1970).

    Google Scholar 

  23. A. V. Anisimov, V. F. Ionova, V. K. Govorek, V. S. Babaitsev, and E. A. Viktorova, Dokl. Akad. Nauk SSSR,244, 362 (1979).

    Google Scholar 

  24. T. Takahashi, A. Kaji, and Yun-ichi-Hayami, Bull. Inst. Chem. Res. Kyoto Univ.,51, 163 (1973).

    Google Scholar 

  25. H. Kwart and N. A. Johnson, J. Am. Chem. Soc.,92, 6064 (1970).

    Google Scholar 

  26. H. Kwart and N. H. Cohen, Chem. Commun., No. 6, 319 (1968).

    Google Scholar 

  27. T. A. Danilova, L. V. Sitnikova, T. Abdin, and E. A. Viktorova, Vestn. Mosk. Univ., Ser. 2, Khim.,17, 591 (1976).

    Google Scholar 

  28. A. V. Anisimov, V. F. Ionova, V. S. Babaitsev, V. K. Govorek, and E. A. Viktorova, Khim. Geterotsikl. Soedin., No. 8, 1062 (1979).

    Google Scholar 

  29. A. V. Anisimov, V. F. Ionova, and E. A. Viktorova, Vestn. Mosk. Univ. Ser. 2, Khim.,19, 729 (1978).

    Google Scholar 

  30. J. Makisumi and A. Murabayashi, Tetrahedron Lett., No. 24, 1971 (1969).

    Google Scholar 

  31. J. Makisumi and A. Sasatani, Tetrahedron Lett., No. 24, 1975 (1969).

    Google Scholar 

  32. J. Makisumi and A. Murabayshi, Tetrahedron Lett., No. 29, 2449 (1969).

    Google Scholar 

  33. J. Makisumi and A. Murabayashi, Tetrahedron Lett., No. 29, 2453 (1969).

    Google Scholar 

  34. A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen, London (1962).

    Google Scholar 

  35. F. G. Bordwell and G. D. Copper, J. Am. Chem. Soc.,74, 1058 (1952).

    Google Scholar 

  36. N. Kharasch, Organic Sulfur Compounds, Pergamon, Oxford, Vol. 1 (1961), p. 97.

    Google Scholar 

  37. T. McAllan and T. W. Cullum, J. Am. Chem. Soc.,73, 3627 (1951).

    Google Scholar 

  38. A. A. Oswald and F. Noel, J. Org. Chem.,26, 3948 (1961).

    Google Scholar 

  39. A. A. Oswald, F. Noel, and A. J. Stephenson, J. Org. Chem.,26, 3969 (1961).

    Google Scholar 

  40. J. F. Baldwin, Chem. Commun., No. 18, 734 (1976).

    Google Scholar 

  41. A. V. Anisimov, V. F. Ionova, V. S. Babaitsev, and E. A. Viktorova, Zh. Org. Khim.,15, 882 (1979).

    Google Scholar 

  42. B. Gopalan, K. Rajagopalan, S. Swaminatham, and K. K. Balasubramanian, Synthesis, No. 4, 409 (1976).

    Google Scholar 

  43. S. Khushvakhtova, A. N. Korepanov, T. A. Danilova, and E. A. Viktorova, Vestn. Mosk. Univ. Ser. 2, Khim.,13, 574 (1972).

    Google Scholar 

  44. E. N. Karaulova, G. D. Gal'pern, V. D. Nikitina, and I. V. Cherepanova, Neftekhimiya,7, 774 (1967).

    Google Scholar 

  45. W. K. Anderson, E. J. LaVoic, and J. C. Battaro, J. Chem. Soc. Perkin Trans. I, No. 1, 1 (1976).

    Google Scholar 

  46. Y. Makisumi, S. Takada, and Y. Matsukara, Chem. Commun., No. 20, 850 (1974).

    Google Scholar 

  47. H. Kwart and T. J. George, Chem. Commun., No. 7, 433 (1970).

    Google Scholar 

  48. L. Brandsma and H. J. Bos, Rec. Trav. Chim.,88, 732 (1969).

    Google Scholar 

  49. L. Brandsma and D. Shuij1-Laros, Rec. Trav. Chim.,89, 110 (1970).

    Google Scholar 

  50. L. Brandsma, P. J. W. Schuijl, D. Schuijl-Laros, J. Mejer, and H. E. Wijers, Int. J. Sulfur Chem.,68, 85 (1971).

    Google Scholar 

  51. K. K. Balasubramanian and B. Venugopalan, Tetrahedron Lett., No. 31, 2643, 2645 (1974).

    Google Scholar 

  52. K. C. Majumdar and B. S. Thyagarajan, Chem. Commun., No. 2, 83 (1972).

    Google Scholar 

  53. Y. Makisumi and S. Takada, Chem. Commun., No. 20, 848 (1974).

    Google Scholar 

  54. S. Khushvakhtova, E. A. Viktorova, and T. A. Danilova, Vestn. Mosk. Univ., Ser. 2, Khim.,10, 99 (1969).

    Google Scholar 

  55. A. E. Perry, J. Phys. Chem.,69, 211 (1965).

    Google Scholar 

  56. E. A. Karakhanov, V. P. Galkin, A. V. Anisimov, A. G. Debov, and E. A. Viktorova, Zh. Fiz. Khim.,41, 977 (1977).

    Google Scholar 

  57. S. Khushvakhtova, E. A. Viktorova, and T. A. Danilova, Vestn. Mosk. Univ., Ser. 2, Khim.,14, 97 (1973).

    Google Scholar 

  58. T. Abdin, T. A. Danilova, and E. A. Viktorova, Khim. Geterotsikl. Soedin., No. 10, 1337 (1973).

    Google Scholar 

  59. G. Dzhamalova, T. A. Danilova, and E. A. Viktorova, Zh. Org. Khim.,12, 76 (1976).

    Google Scholar 

  60. A. N. Korepanov, T. A. Danilova, E. A. Viktorova, and L. M. Sladkova, Vestn. Mosk. Univ., Ser. 2, Khim.,14, 379 (1973).

    Google Scholar 

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, USSR

    A. V. Anisimov & E. A. Viktorova

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  1. A. V. Anisimov
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  2. E. A. Viktorova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–449, April, 1980.

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Anisimov, A.V., Viktorova, E.A. Thio-claisen rearrangement in the synthesis of sulfur-containing heterocyclic compounds (review). Chem Heterocycl Compd 16, 321–333 (1980). https://doi.org/10.1007/BF00552768

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  • DOI: https://doi.org/10.1007/BF00552768

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