Skip to main content
SpringerLink
Log in

Important principle in the chemistry of heterocycles: Electrophilic reactions of compounds of the pentadienyl anion type (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on the electrocyclic reactions of heteroanalogs of the pentadienyl anion that contain heteroatoms in various positions of the five-membered system are correlated.

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. H. Reimlinger, Chem. Ber., 103, 1900 (1970).

    Google Scholar 

  2. J. Elguero, Bull. Soc. Chim. Fr., No. 5, 1925 (1971).

    Google Scholar 

  3. R. B. Woodward and R. Hoffmann, J. Am. Chem. Soc., 87, 395 (1965).

    Google Scholar 

  4. R. B. Woodward and R. Hoffmann, Angew. Chem., 81, 797 (1969).

    Google Scholar 

  5. H. C. Longuet-Higgins and E. W. Abrahamson, J. Am. Chem. Soc., 87, 2045 (1965).

    Google Scholar 

  6. H. E. Zimmerman, Acc. Chem. Res., 4, 272 (1971).

    Google Scholar 

  7. M. J. S. Dewar, Angew. Chem., 83, 859 (1971).

    Google Scholar 

  8. R. B. Bates and D. A. McCombs, Tetrahedron Lett., No. 15, 977 (1969).

    Google Scholar 

  9. M. A. Laurent, Compt. Rend., 19, 353 (1844).

    Google Scholar 

  10. D. H. Hunter, S. K. Sim, and R. P. Steiner, Can. J. Chem., 55, 1229 (1977).

    Google Scholar 

  11. D. R. Hunter and R. P. Steiner, Can. J. Chem., 53, 355 (1975).

    Google Scholar 

  12. G. J. Heiszwolf and H. Kloosterziel, Rec. Trav. Chim., 86, 807 (1967).

    Google Scholar 

  13. D. H. Hunter, R. E. Klinck, R. P. Steiner, and J. B. Stothers, Can. J. Chem., 54, 1464 (1976).

    Google Scholar 

  14. H. Kloosterziel, J. A. A. van Drunen, and P. Galama, Chem. Commun., No. 15, 855 (1969).

    Google Scholar 

  15. H. Kloosterziel and J. A. A. van Drunen, Tetrahedron Lett., No. 13, 1023 (1973).

    Google Scholar 

  16. R. Huisgen and K. Niklas, unpublished data.

  17. K. Niklas, Ph. D. Thesis, University of Munich (1975).

  18. L. Claisen, Ber., 59, 144 (1926).

    Google Scholar 

  19. R. R. Schmidt, W. J. W. Mayer, and H.-U. Wagner, Ann., 2010 (1973).

  20. K. von Auwers and P. Heimke, Ann., 458, 186 (1927).

    Google Scholar 

  21. K. von Auwers and V. Meyer, Ber., 21, 2806 (1888).

    Google Scholar 

  22. R. Huisgen, Angew. Chem., 75, 604 (1963).

    Google Scholar 

  23. R. Huisgen, J. Org. Chem., 41, 403 (1976).

    Google Scholar 

  24. E. C. Taylor and I. J. Turchi, Chem. Rev., 79, 181 (1979).

    Google Scholar 

  25. J. C. Pommelet and J. Chuche, Can. J. Chem., 54, 1571 (1976).

    Google Scholar 

  26. E. Pohjala, Tetrahedron Lett., No. 25, 2585 (1972).

    Google Scholar 

  27. F. Texier and R. Carrié, Bull. Soc. Chim. France, No. 11, 4119 (1971).

    Google Scholar 

  28. E. Fahr, K. Döppert, and F. Scheckenbach, Ann., 696, 136 (1966).

    Google Scholar 

  29. R. Criegee and M. Lederer, Ann., 583, 29 (1953).

    Google Scholar 

  30. D. W. Adamson and J. Kenner, J. Chem. Soc., No. 2, 286 (1935).

    Google Scholar 

  31. C. D. Hurd and S. C. Liu, J. Am. Chem. Soc., 57, 2656 (1935).

    Google Scholar 

  32. J. L. Brewbaker and H. Hart, J. Am. Chem. Soc., 91, 711 (1969).

    Google Scholar 

  33. R. Huisgen, H. Stangl, H. J. Sturm, and H. Wagenhofer, Angew. Chem., 74, 31 (1962).

    Google Scholar 

  34. R. Huisgen, H. Stangl, H. J. Sturm, R. Raab, and K. Bunge, Chem. Ber., 105, 1258 (1978).

    Google Scholar 

  35. N. Engel and W. Steglich, Angew. Chem., 90, 719 (1978).

    Google Scholar 

  36. B. Singh and E. F. Ullman, J. Am. Chem. Soc., 89, 6911 (1967).

    Google Scholar 

  37. B. Singh, A. Zweig, and J. B. Gallivan, J. Am. Chem. Soc., 94, 1199 (1972).

    Google Scholar 

  38. R. Huisgen, J. Sauer, H. J. Sturm, and J. H. Markgraf, Chem. Ber., 93, 2106 (1960).

    Google Scholar 

  39. R. Huisgen and H. J. Sturm, unpublished data.

  40. H. J. Sturm, Ph. D. Thesis, University of Munich (1960).

  41. R. Huisgen, J. Sauer, and M. Seidel, Chem. Ber., 93, 2885 (1960).

    Google Scholar 

  42. G. D. Buckley and W. J. Levy, J. Chem. Soc., No. 11, 3016 (1951).

    Google Scholar 

  43. L. Wolff, Ann., 333, 1 (1904).

    Google Scholar 

  44. L. Wolff and R. Krüche, Ann., 364 48 (1912).

    Google Scholar 

  45. O. Dimroth, Ann., 364, 183 (1909).

    Google Scholar 

  46. O. Dimroth, Ann., 373, 336 (1910).

    Google Scholar 

  47. E. Lieber, C. N. R. Rao, and T. S. Chao, J. Am. Chem. Soc., 79, 5962 (1957).

    Google Scholar 

  48. J. Thiele, Ann., 270, 1, 54 (1892).

    Google Scholar 

  49. J. H. Boyer and E. Miller, J. Am. Chem. Soc., 81, 4671 (1959).

    Google Scholar 

  50. C. Temple and J. A. Montgomery, J. Org. Chem., 30, 826 (1965).

    Google Scholar 

  51. M. Tišler, Synthesis, No. 3, 123 (1973).

    Google Scholar 

  52. R. N. Butler, Adv. Heterocycl. Chem., 21, 402 (1977).

    Google Scholar 

  53. R. Huisgen and I. Ugi, Chem. Ber., 90, 2914 (1957).

    Google Scholar 

  54. I. Ugi and R. Huisgen, Chem. Ber., 91, 531 (1958).

    Google Scholar 

  55. O. L. Chapman, G. L. Eian, A. Bloom, and J. Clardy, J. Am. Chem. Soc., 93, 2918 (1971).

    Google Scholar 

  56. A. G. Schultz and W. K. Hagmann, Chem. Commun., No. 18, 726 (1976).

    Google Scholar 

  57. A. G. Schultz and M. B. De Tar, J. Am. Chem. Soc., 98, 3564 (1976).

    Google Scholar 

  58. A. E. Chichibabin (Tschitschibabin), Ber., 60, 1607 (1927).

    Google Scholar 

  59. H. Beyer, E. Bulka, and F. W. Beckhaus, Chem. Ber., 92, 2593 (1959).

    Google Scholar 

  60. W. D. Ollis and C. A. Ramsden, Adv. Heterocycl. Chem., 19, 1, 13 (1976).

    Google Scholar 

  61. H. O. Bayer, R. Huisgen, R. Knorr, and F. C. Schaefer, Chem. Ber., 103, 2581 (1970).

    Google Scholar 

  62. E. Funke and R. Huisgen, Chem. Ber., 104, 3222 (1971).

    Google Scholar 

  63. R. Huisgen and E. Funke, Angew. Chem., 79, 320 (1967).

    Google Scholar 

  64. R. Huisgen, E. Funke, H. Gotthardt, and H.-L. Panke, Chem. Ber., 104, 1532 (1971).

    Google Scholar 

  65. R. Huisgen, E. Funke, F. C. Schaefer, H. Gotthardt, and E. Brunn, Tetrahedron Lett., No. 19, 1809 (1967).

    Google Scholar 

  66. E. Funke, R. Huisgen, and F. C. Schaefer, Chem. Ber., 104, 1550 (1971).

    Google Scholar 

  67. E. Brunn, E. Funke, H. Gotthardt, and R. Huisgen, Chem. Ber., 104, 1562 (1971).

    Google Scholar 

  68. H. Prinzbach and H. Babsch, Angew. Chem., 87, 772 (1975).

    Google Scholar 

  69. W. Eberbach, M. Perroud-Argüelles, H. Achenbach, E. Druckrey, and H. Prinzbach, Helv. Chim. Acta, 54, 2579 (1971).

    Google Scholar 

  70. L. J. Chapelle, J. Elguero, R. Jacquier, and G. Tarrago, Bull. Soc. Chim. France, No. 9, 3147 (1970).

    Google Scholar 

  71. R. Stollé, Ber., 32, 797 (1899).

    Google Scholar 

  72. F. D. Popp, J. Chem. Soc., No. 9, 3503 (1964).

    Google Scholar 

  73. H. Behringer, D. Bender, J. Falkenberg, and R. Wiedenmann, Chem. Ber., 101, 1428 (1968).

    Google Scholar 

  74. J. Goerdeler, R. Büchler, and S. Solyom, Chem. Ber., 110, 285 (1977).

    Google Scholar 

  75. A. Padwa, J. Smolanoff, and A. Tremper, J. Org. Chem., 41, 453 (1976).

    Google Scholar 

  76. P. A. S. Smith and B. B. Brown, J. Am. Chem. Soc., 73, 2435 (1951).

    Google Scholar 

  77. R. Huisgen, J. Sauer, H. J. Sturm, and J. H. Markgraf, Chem. Ber., 93, 2106 (1960).

    Google Scholar 

  78. T. Zincke and P. Schwarz, 307, 28 (1899).

  79. G. Englert, Z. Elektrochem., Angew. Phys. Chem., 65, 854 (1961).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. University of Munich, Munich, Germany

    R. Huisgen

Authors
  1. R. Huisgen
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Lecture given at the First European Symposium on Organic Chemistry in Cologne, West Germany, on August 21, 1979.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 579–598, May, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Huisgen, R. Important principle in the chemistry of heterocycles: Electrophilic reactions of compounds of the pentadienyl anion type (review). Chem Heterocycl Compd 17, 417–433 (1981). https://doi.org/10.1007/BF00505680

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00505680

Keywords

Search

Navigation