Skip to main content
SpringerLink
Log in

Use of sulfonium ylides in the synthesis of heterocyclic systems (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature on the use of sulfur ylides in the synthesis of heterocyclic systems of varied structure is reviewed. The possible preparative value of these reactions is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. A. W. Johnson and R. B. La Count, Chem. Ind., No. 4, 1440 (1958).

    Google Scholar 

  2. A. W. Johnson and R. B. La Count, J. Am. Chem. Soc., 83, 417 (1961).

    Google Scholar 

  3. V. Franzen, and H.-E. Driessen, Tetrahedron Lett., No. 15, 661 (1962).

    Google Scholar 

  4. E. D. Corey and M. Chaykowsky, J. Am. Chem. Soc., 84, 867 (1962).

    Google Scholar 

  5. E. D. Corey and M. Chaykowsky, J. Am. Chem. Soc., 84, 3782 (1962).

    Google Scholar 

  6. E. D. Corey and M. Chaykowsky, J. Am. Chem. Soc., 87, 1353 (1965).

    Google Scholar 

  7. V. Franzen and H.-E. Driessen, Chem. Ber., 96, 1881 (1963).

    Google Scholar 

  8. A. W. Johnson, V. J. Hruby, and J. S. Williams, J. Am. Chem. Soc., 86, 917 (1964).

    Google Scholar 

  9. E. D. Corey and W. Oppolzer, J. Am. Chem. Soc., 86, 1899 (1964).

    Google Scholar 

  10. E. D. Corey, M. Jautelat, and W. Oppolzer, Tetrahedron Lett., No. 24, 2325 (1967).

    Google Scholar 

  11. K. W. Ratts and A. N. Yao, J. Org. Chem., 31, 1185 (1966).

    Google Scholar 

  12. B. M. Trost, J. Am. Chem. Soc., 89, 138 (1967).

    Google Scholar 

  13. M. Takaku, Y. Hayashi, and H. Nozaki, Tetrahedron, 26, 1243 (1970).

    Google Scholar 

  14. A. W. Johnson and R. T. Amel, Tetrahedron Lett., No. 8, 819 (1966).

    Google Scholar 

  15. A. W. Johnson and R. T. Amel, J. Org. Chem., 34, 1240 (1969).

    Google Scholar 

  16. J. L. Pierre, R. Guidotty, and P. Arnaud, Bull. Soc. Chim. France, No. 4, 1439 (1967).

    Google Scholar 

  17. G. B. Payne, J. Org. Chem., 33, 3517 (1968).

    Google Scholar 

  18. C. W. Schimelpfenig and J. A. Ruder, Chem. Eng. Data, 14, 133 (1969).

    Google Scholar 

  19. K. K. Andersen, J. Chem. Soc. Chem. Commun., No. 18, 1051 (1971).

    Google Scholar 

  20. K. K. Andersen, M. Cinquini, and N. E. Papanikolaou, J. Org. Chem., 35, 706 (1970).

    Google Scholar 

  21. B. M. Trost and R. F. Hammen, J. Am. Chem. Soc., 95, 962 (1973).

    Google Scholar 

  22. C. R. Johnson, E. R. Janiga, and M. Haake, J. Am. Chem. Soc., 90, 3890 (1968).

    Google Scholar 

  23. C. R. Johnson, M. Haake, and C. W. Schroeck, J. Am. Chem. Soc., 92, 6594 (1970).

    Google Scholar 

  24. C. R. Johnson and P. R. Rogers, J. Org. Chem., 38, 1793 (1973).

    Google Scholar 

  25. C. R. Johnson and C. W. Schroeck, J. Am. Chem. Soc., 95, 7418 (1973).

    Google Scholar 

  26. C. R. Johnson, C. W. Schroeck, and J. R. Shanklin, J. Am. Chem. Soc., 95, 7424 (1973).

    Google Scholar 

  27. C. R. Johnson and C. W. Schroeck, J. Am. Chem. Soc., 90, 6852 (1968).

    Google Scholar 

  28. C. R. Johnson and L. J. Pepoy, J. Org. Chem., 37, 671 (1972).

    Google Scholar 

  29. C. R. Johnson, G. F. Katekar, R. F. Huxol, and E. R. Janiga, J. Am. Chem. Soc., 93, 3771 (1971).

    Google Scholar 

  30. M. J. Bogdanovizc and B. M. Trost, Tetrahedron Lett., No. 10, 887 (1972).

    Google Scholar 

  31. P. Bravo and G. Gaviraghi, Gazz. Chim. Ital., 104, 1307 (1974).

    Google Scholar 

  32. P. Bravo and G. Gaviraghi, J. Heterocycl. Chem., 14, 37 (1977).

    Google Scholar 

  33. K. Tokuno, F. Miyoshi, J. Arata, J. Itatani, J. Arakawa, and T. Ohashi, Yakugaku Zasshi, 98, 1005 (1978); Chem. Abstr., 90, 6195 (1978).

    Google Scholar 

  34. P. Cazeau and B. Muckensturm, Tetrahedron Lett., No. 17, 1493 (1977).

    Google Scholar 

  35. M. E. Garst and A. T. Johnson, Tetrahedron Lett., 21, 4811 (1980).

    Google Scholar 

  36. M. E. Garst, J. Org. Chem., 44, 1578 (1979).

    Google Scholar 

  37. O. Tsuge and I. Shinkai, Bull. Chem. Soc. Jpn., 43, 3514 (1970).

    Google Scholar 

  38. E. D. Corey and S. Nozoe, J. Am. Chem. Soc., 85, 3527 (1963).

    Google Scholar 

  39. G. Drefahl, K. Ponsold, and H. Schick, Chem. Ber., 97, 3529 (1964).

    Google Scholar 

  40. R. S. Tewari, A. K. Awasthi, and A. Awasthi, Synthesis, No. 4, 330 (1983).

    Google Scholar 

  41. C. R. Johnson and J. P. Lockard, Tetrahedron Lett., No. 48, 4589 (1971).

    Google Scholar 

  42. R. Huisgen, C. Fulka, I. Kalwinsch, Xingua Li, G. Mloston, J. Morgan, and A. Probste, Bull. Soc. Chim. Belges, 93, 511 (1984).

    Google Scholar 

  43. R. M. Kellog, M. Noteboom, and J. K. Kaiser, J. Org. Chem., 40, 2573 (1975).

    Google Scholar 

  44. Xigya Li and R. Huisgen, Tetrahedron Lett., No. 23, 4181 (1983).

    Google Scholar 

  45. Y. Hayashi, T. Akazama, K. Yamamoto, and R. Oda, Tetrahedron Lett., No. 21, 1781 (1971).

    Google Scholar 

  46. Y. Hayashi, H. Nakamura, and H. Nozaki, Bull. Chem. Soc. Jpn., 46, 667 (1973).

    Google Scholar 

  47. M. Hory, T. Kataoka, H. Shimizu, and M. Okitsu, Heterocycles, 16, 721 (1981).

    Google Scholar 

  48. K. Okuma, J. Tanaka, S. Kaji, and H. Ohta, J. Org. Chem., 48, 5133 (1983).

    Google Scholar 

  49. M. Vaultier, R. Danion-Bougot, D. Danion, J. Hamelin, and R. Carrie, Tetrahedron Lett., No. 22, 1923 (1973).

    Google Scholar 

  50. M. Vaultier, R. Danion-Bougot, D. Danion, J. Hamelin, and R. Carrie, J. Org. Chem., 40, 2990 (1975).

    Google Scholar 

  51. U. K. Nadir and V. K. Koul, Synthesis, No. 7, 554 (1983).

    Google Scholar 

  52. A. Umani-Ronchi, P. Bravo, and G. Gaudiano, Tetrahedron Lett., No. 29, 3477 (1966).

    Google Scholar 

  53. P. Bravo, G. Gaudiano, and A. Umani-Ronchi, Chim. Ind., 49, 286 (1967).

    Google Scholar 

  54. P. Bravo, G. Gaudiano, and A. Umani-Ronchi, Gazz. Chim. Ital., 97, 1664 (1967).

    Google Scholar 

  55. G. Gaudiano, P. P. Ponti, and A. Umani-Ronchi, Gazz. Chim. Ital., 98, 48 (1968).

    Google Scholar 

  56. Y. Nakada, T. Hata, C. Tamura, T. Iwaoka, M. Kondo, and J. Ide, Tetrahedron Lett., 22, 473 (1981).

    Google Scholar 

  57. G. Gaudiano, A. Umani-Ronchi, P. Bravo, and M. Acampora, Tetrahedron Lett., No. 2, 107 (1967).

    Google Scholar 

  58. Y. Hayashi and R. Oda, Tetrahedron Lett., No. 11, 853 (1969).

    Google Scholar 

  59. Y. Hayashi, T. Watanabe, and R. Oda, Tetrahedron Lett., No. 8, 606 (1970).

    Google Scholar 

  60. G. Gaudiano, C. Ticozzi, A. Umani-Ronchi, and P. Bravo, Gazz. Chim. Ital., 97, 1411 (1967).

    Google Scholar 

  61. E. Van Loock, G. L'abbe, and G. Smets, J. Org. Chem., 36, 2520 (1971).

    Google Scholar 

  62. E. Van Loock, G. L'abbe, and G. Smets, Tetrahedron, 28, 3061 (1972).

    Google Scholar 

  63. G. L'abbe, G. Mathys, and S. Toppet, Chem. Ind., No. 6, 278 (1975).

    Google Scholar 

  64. M. Higo and T. Mukaiyama, Tetrahedron Lett., No. 29, 2565 (1970).

    Google Scholar 

  65. M. Takaku, Y. Hayashi, and H. Nozaki, Tetrahedron Lett., No. 25, 2053 (1969).

    Google Scholar 

  66. H. Hayashi, M. Kobayashi, and H. Nozaki, Tetrahedron, 26, 4353 (1970).

    Google Scholar 

  67. M. Takebayashi, T. Kitashoju, F. Nagaoka, and H. Ueda, Kinki Daigaku Rikogabubu Kenkyu Hikoku, No. 16, 25 (1981); Chem. Abstr., 96, 203646 (1981).

    Google Scholar 

  68. H. Takei and T. Mukaiyama, Bull. Chem. Soc. Jpn., 43, 3607 (1970).

    Google Scholar 

  69. T. Mukaiyama, M. Higo, and T. Sacashita, Tetrahedron Lett., No. 40, 3697 (1971).

    Google Scholar 

  70. T. Mukaiyama, M. Higo, and H. Takei, Bull. Chem. Soc. Jpn., 43, 2566 (1970).

    Google Scholar 

  71. J. K. Batty, P. D. Howes, and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., No. 11, 534 (1971).

    Google Scholar 

  72. H. König, H. Metzger, and K. Sulert, Chem. Ber., 98, 3712 (1965).

    Google Scholar 

  73. M. Clagett, A. Gooch, P. Graham, N. Holy, B. Mains, and J. Strunk, J. Org. Chem., 41, 4043 (1976).

    Google Scholar 

  74. T. Sakakibara and R. Sudoh, J. Chem. Soc. Chem. Commun., No. 1, 7 (1977).

    Google Scholar 

  75. T. Sakakibara, R. Sudoh, and T. Nakagawa, Bull. Chem. Soc. Jpn., 51, 1189 (1978).

    Google Scholar 

  76. T. Sakakibara and R. Sudoh, Bull. Chem. Soc. Jpn., 51, 1193 (1978).

    Google Scholar 

  77. P. Bravo, G. Gaudiano, C. Ticozzi, and A. Umani-Ronchi, J. Chem. Soc. Chem. Commun., No. 21, 1311 (1968).

    Google Scholar 

  78. P. Bravo, G. Gaudiano, C. Ticozzi, and A. Umani-Ronchi, Gazz. Chim. Ital., 99, 549 (1969).

    Google Scholar 

  79. P. Bravo, G. Gaudiano, P. P. Ponti, and C. Ticozzi, Tetrahedron, 28, 3485 (1972).

    Google Scholar 

  80. P. Bravo and C. Ticozzi, Gazz. Chim. Ital., 105, 91 (1975).

    Google Scholar 

  81. O. Tsuge, A. Sakai, and M. Tashiro, Tetrahedron, 29, 1983 (1973).

    Google Scholar 

  82. P. Dalla Croce, Ann. Chim., 63, 895 (1973).

    Google Scholar 

  83. G. B. Payne, J. Org. Chem., 32, 3351 (1967).

    Google Scholar 

  84. Y. Tamura, H. Taniguchi, T. Miyamoto, N, Tsunekawa, and M. Ikeda, J. Org. Chem., 39, 3519 (1974).

    Google Scholar 

  85. P. Bravo, G. Gaudiano, and C. Ticozzi, Gazz. Chim. Ital., 102, 395 (1972).

    Google Scholar 

  86. B. M. Trost, R. C. Atkins, and L. Hoffmann, J. Am. Chem. Soc., 95, 1285 (1973).

    Google Scholar 

  87. I. Kalvinsch and R. Huisgen, Tetrahedron Lett., No. 40, 3941 (1981).

    Google Scholar 

  88. H. Nozaki, M. Takaku, Y. Hayashi, and K. Kondo, Tetrahedron, 24, 6563 (1968).

    Google Scholar 

  89. J. Terao, M. Tanaka, M. Imai, and K. Achiva, Tetrahedron Lett., No. 25, 3011 (1985).

    Google Scholar 

  90. M. Aono, C. Hyodo, J. Terao, and K. Achiva, Tetrahedron Lett., No. 34, 4039 (1986).

    Google Scholar 

  91. C. R. Johnson and P. E. Rogers, J. Org. Chem., 38, 1798 (1973).

    Google Scholar 

  92. C. R. Johnson, J. Lockard, and E. Kennedy, J. Org. Chem., 45, 264 (1980).

    Google Scholar 

  93. M. Yamamoto, J. Chem. Soc., Perkin Trans, 1, No. 16, 1688 (1976).

    Google Scholar 

  94. M. Watanabe, M. Baba, T. Kinoshita, and S. Furukawa, Chem. Pharm. Bull., 24, 2421 (1976).

    Google Scholar 

  95. T. Nishio, M. Sugawara, and J. Omore, J. Heterocycl. Chem., 16, 815 (1979).

    Google Scholar 

  96. C. M. Harris, J. C. Cleary, and T. M. Harris, J. Org. Chem., 39, 72 (1974).

    Google Scholar 

  97. M. Takebayashi, H. Matsuji, and J. Hirata, Kinki Daigaku Rikogabubu Kenkyu Hikoku, No. 17, 33 (1982); Chem. Abstr., 97, 181389 (1982).

    Google Scholar 

  98. M. O. Lozinskii, S. N. Kukota, V. N. Bondar, and P. S. Pel'kis, Zh. Org. Khim., 9, 216 (1973).

    Google Scholar 

  99. O. Tsuge and M. Koga, Org. Prep. Proc. Int., 7, 173 (1975).

    Google Scholar 

  100. A. B. Hortmann, J. Am. Chem. Soc., 87, 4972 (1965).

    Google Scholar 

  101. A. B. Hortmann and R. L. Harris, J. Am. Chem. Soc., 93, 2471 (1971).

    Google Scholar 

  102. Y. Tamura, T. Miyamoto, H. Taniguchi, M. Tsunekawa, and M. Ikeda, J. Org. Chem., 39, 3519 (1974).

    Google Scholar 

  103. M. Watanabe, T. Kinoshita, and S. Furukawa, Chem. Pharm. Bull., 23, 258 (1975).

    Google Scholar 

  104. Y. Kishida and J. Ide, Chem. Pharm. Bull., 15, 360 (1967).

    Google Scholar 

  105. B. Holt, J. Howard, and P. A. Lowe, Tetrahedron Lett., No. 56, 4937 (1969).

    Google Scholar 

  106. H. Nozaki, D. Tunemoto, S. Matubara, and K. Kondo, Tetrahedron, 23, 545 (1967).

    Google Scholar 

  107. Y. Hayashi and H. Nozaki, Tetrahedron, 27, 3085 (1971).

    Google Scholar 

  108. T. Eicher, E. Angerer, and A.-M. Hansen, Liebigs Ann., 746, 102 (1971).

    Google Scholar 

  109. K. Tanaka, Y. Hayashi, and A. Kaji, Phosph. Sulf., 16, 201 (1983).

    Google Scholar 

  110. M. Yoshimoto and Y. Kishida, Chem. Pharm. Bull., 18, 2518 (1970).

    Google Scholar 

  111. S. Ueda, Y. Hayashi, and R. Oda, Tetrahedron Lett., No. 56, 4967 (1969).

    Google Scholar 

  112. T. Kinoshita, T. Onoue, M. Watanabe, and S. Furukawa, Chem. Pharm. Bull., 28, 795 (1980).

    Google Scholar 

  113. R. Faragher, T. L. Gilchrist, and I. W. Southon, Tetrahedron Lett., No. 42, 4113 (1979).

    Google Scholar 

  114. V. Cere, C. Paolucci, E. Sandri, and A. Fava, J. Chem. Soc., Chem. Commun., No. 16, 755 (1980).

    Google Scholar 

  115. E. Vedejs and J. P. Hagen, J. Am. Chem. Soc., 97, 6878 (1965).

    Google Scholar 

  116. M. Hory, T. Kataoka, H. Simizu, K. Marita, S. Ohno, and H. Aoki, Chem. Lett., No. 9, 1109 (1974).

    Google Scholar 

  117. P. Bravo, G. Gaudiano, and A. Umani-Ronchi, Tetrahedron Lett., No. 9, 679 (1969).

    Google Scholar 

  118. P. Bravo, G. Gaudiano, and A. Umani-Ronchi, Gazz. Chim. Ital., 100, 652 (1970).

    Google Scholar 

  119. H. Junjappa, Synthesis, No. 12, 799 (1975).

    Google Scholar 

  120. P. G. Gassman, T. J. Van Bergen, D. P. Gilbert, and B. W. Cue, J. Am. Chem. Soc., 96, 5495 (1974).

    Google Scholar 

  121. P. G. Gassman and T. J. Van Bergen, J. Am. Chem. Soc., 96, 5508 (1974).

    Google Scholar 

  122. M. Watanabe, M. Kodera, T. Kinoshita, and S. Furukawa, Chem. Pharm. Bull., 23, 2598 (1975).

    Google Scholar 

  123. M. Chaykovsky, L. Benjamin, R. I. Fryer, and W. Metlesics, J. Org. Chem., 35, 1178 (1970).

    Google Scholar 

  124. T. Kunieda and B. Witkop, J. Am. Chem. Soc., 91, 7752 (1969).

    Google Scholar 

  125. K. Okuma, N. Higuchi, H. Ohta, and M. Kobayashi, Chem. Lett., No. 12, 1503 (1980).

    Google Scholar 

  126. P. G. Gassmann and G. D. Gruetzmacher, J. Am. Chem. Soc., 96, 5487 (1974).

    Google Scholar 

  127. T. L. Gilchrist and G. M. Iskander, J. Chem. Soc. Perkin Trans. 1, No. 3, 831 (1982).

    Google Scholar 

  128. P. Bravo, G. Gaudiano, and M. G. Zubiani, J. Heterocycl. Chem., 7, 967 (1970).

    Google Scholar 

  129. M. Nori, T. Kataoka, H. Shimizu, and M. Okitsu, Tetrahedron Lett., 21, 4287 (1980).

    Google Scholar 

  130. B. Holt and P. A. Lowe, Tetrahedron Lett., No. 7, 683 (1966).

    Google Scholar 

  131. P. Bravo, G. Gaudiano, and C. Ticozzi, Gazz. Chim. Ital., 103, 95 (1973).

    Google Scholar 

  132. L. Cadona and P. Dalla Croce, Synthesis, No. 12, 800 (1976).

    Google Scholar 

  133. E. Breuer and D. Melumad, Tetrahedron Lett., No. 23, 1875 (1969).

    Google Scholar 

  134. H.-G. Lehmann, Tetrahedron Lett., No. 5, 607 (1968).

    Google Scholar 

  135. M. S. Newman and Lee Len-Fang, J. Org. Chem., 39, 1446 (1974).

    Google Scholar 

  136. T. Mukaiyama, K. Hagio, H. Takei, and K. Saigo, Bull. Chem. Soc. Jpn., 44, 161 (1971).

    Google Scholar 

  137. M. C. Sacquet, B. Graffe, and P. Maitte, Tetrahedron Lett., 43, 4453 (1972).

    Google Scholar 

  138. E. Block and M. Haake, Organic Compounds of S, Se, Te, 4, 78 (1977).

    Google Scholar 

  139. R. Huisgen, C. Fulka, and Y. Kalwinsch, Bull. Soc. Chim. Belges, 93, 511 (1984).

    Google Scholar 

  140. Yu. G. Gololobow, A. N. Nesmejanov, V. P. Lysenko, and I. E. Boldeskul, Tetrahedron, 43, 2609 (1987).

    Google Scholar 

  141. A. Johnson, The Chemistry of Ylides [Russian translation], Mir, Moscow (1969), pp. 324–391.

    Google Scholar 

  142. K. R. Johnson, in: General Organic Chemistry [D. Barton and U. D. Ollis (eds.)] [Russian translation], Khimiya, Moscow (1983), Vol. 5, pp. 403–417.

    Google Scholar 

  143. B. M. Trost and L. S. Melvin, Sulfur Ylides, Acad. Press, New York (1975).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov State University, 119899, Moscow

    N. N. Magdesieva & T. A. Sergeeva

Authors
  1. N. N. Magdesieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. A. Sergeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–173, February, 1990.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Magdesieva, N.N., Sergeeva, T.A. Use of sulfonium ylides in the synthesis of heterocyclic systems (review). Chem Heterocycl Compd 26, 123–145 (1990). https://doi.org/10.1007/BF00499405

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00499405

Keywords

Search

Navigation