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Concept of π-deficiency in the chemistry of heteroaromatic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

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Literature cited

  1. A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 6, 723 (1977).

    Google Scholar 

  2. A. Albert, Heterocyclic Chemistry. An Introduction, Athlone Press, University of London, London (1958); 2nd ed. (1968).

    Google Scholar 

  3. F. Wudl, M. L. Kaplan, B. K. Teo, and J. Marshall, J. Org. Chem., 42, 1666 (1977).

    Google Scholar 

  4. C. Hansch, J. Chem. Educ., 51, 360 (1974).

    Google Scholar 

  5. A. Szent-Györgyi, Introduction to a Submolecular Biology, Academic Press (1960).

  6. M. A. Slifkin, Charge Transfer Interactions of Biomolecules, Academic Press, New York (1971).

    Google Scholar 

  7. H. Sigel and C. F. Naumann, J. Am. Chem. Soc., 98, 730 (1976).

    Google Scholar 

  8. N. E. Giacintov, T. Prusik, and J. M. Khosrofian, J. Am. Chem. Soc., 98, 6444 (1976).

    Google Scholar 

  9. A. Albert and W. L. F. Armarego, Adv. Heterocycl. Chem., 4, 1 (1965).

    Google Scholar 

  10. M. J. Cook, A. R. Katritzky, and P. Linda, Adv. Heterocycl. Chem., 17, 255 (1975).

    Google Scholar 

  11. M. Witanowski, L. Stefaniak, H. Jannszewski, and G. A. Webb, Tetrahedron, 27, 3129 (1971).

    Google Scholar 

  12. A. F. Pozharskii, Dissertation Submitted for the Academic Degree of Doctor of Chemical Sciences, Rostov State Univ., Rostov-on-Don (1972).

    Google Scholar 

  13. R. J. Pugmire and D. M. Grant, J. Am. Chem. Soc., 90, 697 (1968).

    Google Scholar 

  14. T. E. Peacock, J. Chem. Soc., No. 4, 1946 (1960).

    Google Scholar 

  15. P. J. Black, R. D. Brown, and M. L. Heffernan, Aust. J. Chem., 20, 1305 (1967).

    Google Scholar 

  16. J. E. Bloor and D. L. Breen, J. Am. Chem. Soc., 89, 6835 (1967).

    Google Scholar 

  17. J. Almlof, B. Roos, U. Wahlgren, and H. Johanson, J. Electron Spectrosc. Relat. Phenom., 2, 51 (1973).

    Google Scholar 

  18. P. C. Lauterbur, J. Chem. Phys., 43, 360 (1965).

    Google Scholar 

  19. T. Tokuhiro and G. Fraenkel, J. Am. Chem. Soc., 91, 5005 (1969).

    Google Scholar 

  20. R. J. Pugmire, D. M. Grant, M. J. Robins, and R. K. Robins, J. Am. Chem. Soc., 91, 6381 (1969).

    Google Scholar 

  21. E. Lucken, in: A. R. Katritsky, Physical Methods in Heterocyclic Chemistry, Vol. 6, Academic Press (1974).

  22. L. N. Short, J. Chem. Soc., No. 12, 4584 (1952).

    Google Scholar 

  23. L. N. Short, J. Chem. Soc., No. 11, 4200 (1956).

    Google Scholar 

  24. S. F. Mason, J. Chem. Soc, No. 10, 3619 (1958).

    Google Scholar 

  25. J. D. S. Goulden, J. Chem. Soc., No. 7, 2939 (1952).

    Google Scholar 

  26. G. P. Syrova, Dissertation Submitted for the Academic Degree of Candidate of Chemical Sciences, Rostov State Univ., Rostov-on-Don (1973).

    Google Scholar 

  27. O. P. Shkurko, E. P. Khmeleva, S. G. Baram, M. M. Shakirov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 7, 996 (1978).

    Google Scholar 

  28. J. H. Blanch, J. Chem. Soc. B, No. 10, 937 (1966).

    Google Scholar 

  29. A. F. Pozharskii, A. D. Garnovskii, and A. M. Simonov, Usp. Khim., 35, 261 (1966).

    Google Scholar 

  30. V. I. Minkin and B. Ya. Simkin, Khim. Geterotsikl. Soedin., No. 5, 678 (1971).

    Google Scholar 

  31. A. F. Pozharskii, E. N. Malysheva, A. N. Suslov, and L. L. Popova, Khim. Geterotsikl. Soedin., No. 5, 692 (1979).

    Google Scholar 

  32. A. F. Pozharskii and A. M. Simonov, Chichibabin Amination of Heterocycles [in Russian], Rostov State Univ., Rostov-on-Don (1971).

    Google Scholar 

  33. R. J. Pugmire and D. M. Grant. J. Am. Chem. Soc., 90, 4232 (1968).

    Google Scholar 

  34. V. I. Minkin, A. F. Pozharskii, and Yu. A. Ostroumov, Khim. Geterotsikl. Soedin., No. 4, 551 (1966).

    Google Scholar 

  35. M. Begtrup, R. M. Claramunt, and J. Elguero, J. Chem. Soc., Perkin Trans. II, No. 2, 99 (1978).

    Google Scholar 

  36. L. N. Yakhontov, Usp. Khim., 37, 1258 (1968).

    Google Scholar 

  37. G. B. Barlin and D. J. Brown, in: R. N. Castle (editor), Topics in Heterocyclic Chemistry, Wiley, New York (1969), p. 122.

    Google Scholar 

  38. Z. Neimann, Experientia, No. 8, 996 (1975).

    Google Scholar 

  39. O. N. Chupakhin, Dissertation Submitted for the Academic Degree of Doctor of Chemical Sciences, Rostov State Univ., Rostov-on-Don (1977).

    Google Scholar 

  40. H. Balli, B. Hellrung, and H. Hinsken, Helv. Chim. Acta, 57, 1174 (1974).

    Google Scholar 

  41. H. Balli, B. Hellrung, and A. Kneubuhler-Hof, Helv. Chim. Acta, 57, 1178 (1974).

    Google Scholar 

  42. J. Degani, L. Lunazzi, and F. Taddei, Boll. Sci. Fac. Chim. Ind. Bologna, 23, 131 (1965).

    Google Scholar 

  43. S. Yoneda, T. Sugimoto, and Z. Yoshida, Tetrahedron, 29, 2009 (1973).

    Google Scholar 

  44. V. G. Kharchenko, S. N. Chalaya, and T. M. Konovalova, Khim. Geterotskil. Soedin., No. 2, 147 (1975).

    Google Scholar 

  45. A. K. Sheinkman, Dissertation Submitted for the Academic Degree of Doctor of Chemical Sciences, Ros- tov State Univ., Rostov-on-Don (1972).

    Google Scholar 

  46. A. R. Katritzky, C. R. Palmer, F. J. Swinbourne, T. T. Tidwell, and R. D. Topsom, J. Am. Chem. Soc., 91, 636 (1969).

    Google Scholar 

  47. A. R. Katritzky and F. J. Swinbourne, J. Chem. Soc., No. 12, 6707 (1965).

    Google Scholar 

  48. J. Chaudhuri, S. Kume, J. Jagur-Grodzinski, and M. Szwarc, J. Am. Chem. Soc., 90, 6421 (1968).

    Google Scholar 

  49. P. Kasai and D. McLeod, J. Am. Chem. Soc., 95, 27 (1973).

    Google Scholar 

  50. P. H. Kasai and D. McLeod, J. Am. Chem. Soc., 95, 4801 (1973).

    Google Scholar 

  51. J. Nenner and G. J. Schulz, J. Chem. Phys., 62, 1747 (1975).

    Google Scholar 

  52. V. Kalyanaraman, C. N. R. Rao, and M. V. George, J. Chem. Soc. B, No. 12, 2406 (1971).

    Google Scholar 

  53. K. B. Wiberg and T. P. Lewis, J. Am. Chem. Soc., 92, 7154 (1970).

    Google Scholar 

  54. S. Millefiori, J. Heterocycl. Chem., 7, 145 (1970).

    Google Scholar 

  55. O. N. Chupakhin, V. N. Charushin, I. M. Sosonkin, E. G. Kovalev, G. L. Kalb, and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., No. 5, 690 (1977).

    Google Scholar 

  56. A. V. Lizogub and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 1, 110 (1979).

    Google Scholar 

  57. A. V. El'tsov and M. Z. Girshovich, Zh. Org. Khim., 3, 1332 (1967).

    Google Scholar 

  58. V. Kampars and O. Neilands, Usp. Khim., 46, 945 (1977).

    Google Scholar 

  59. V. Kampars and O. Neilands, Zh. Obshch. Khim., 47, 442 (1977).

    Google Scholar 

  60. M. Feldman and S. Winstein, Theor. Chim. Acta, 10, 86 (1968).

    Google Scholar 

  61. H. Inone, S. Hayashi, and E. Imoto, Bull. Chem. Soc. Jpn., 37, 336 (1964).

    Google Scholar 

  62. H. J. Dauben and J. D. Wilson, Chem. Commun., No. 24, 1929 (1968).

    Google Scholar 

  63. R. Zahradnik and J. Koutecky, Adv. Heterocycl. Chem., 5, 69 (1965).

    Google Scholar 

  64. G. Illuminati, Adv. Heterocycl. Chem., 3, 285 (1964).

    Google Scholar 

  65. R. G. Shepherd and J. L. Fedrick, Adv. Heterocycl. Chem., 4, 145 (1965).

    Google Scholar 

  66. V. P. Mamaev, O. A. Zagulyaeva, and S. M. Shein, Khim. Geterotsikl. Soedin., No. 6, 723 (1973).

    Google Scholar 

  67. J. Reed, in: A. R. Katritzky, Physical Methods in Heterocyclic Chemistry, Vol. 6, Academic Press (1974).

  68. J. F. Wolfe, J. C. Greene, and T. Hudlicky, J. Org. Chem., 37, 3198 (1972).

    Google Scholar 

  69. Gy. Simig, H. C. van der Plas, and C. A. Laudheer, Rec. Trav. Chim., 95, 113, 125 (1976).

    Google Scholar 

  70. J. A. Zoltewicz and L. S. Helmick, J. Am. Chem. Soc., 94, 682 (1972).

    Google Scholar 

  71. A. F. Pozharskii, A. M. Simonov, and V. N. Doron'kin, Usp. Khim., 47, 1933 (1978).

    Google Scholar 

  72. V. N. Doron'kin, A. F. Pozharskii, and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 2, 257 (1979).

    Google Scholar 

  73. G. B. Barlin and W. V. Brown, J. Chem. Soc. B, No. 7, 648, 736 (1967).

    Google Scholar 

  74. N. B. Chapman and D. Q. Russell-Hill, J. Chem. Soc., No. 6, 1563 (1956).

    Google Scholar 

  75. J. H. Hill and J. G. Krause, J. Org. Chem., 29, 1642 (1964).

    Google Scholar 

  76. J. H. Hill and J. H. Ehrlich, J. Org. Chem., 36, 3248 (1971).

    Google Scholar 

  77. A. Ricci and P. Vivarelli, Gazz. Chim. Ital., 97, 741 (1967).

    Google Scholar 

  78. A. F. Pozharskii, L. P. Smirnova, A. I. Belyashova, N. N. Zatsepina, and I. F. Tupitsyn, Khim. Geterotsikl. Soedin., No. 7, 961 (1979).

    Google Scholar 

  79. N. N. Zatsepina and I. F. Tupitsyn, Khim. Geterotsikl. Soedin., No. 12, 1587 (1974).

    Google Scholar 

  80. G. Klopman, J. Am. Chem. Soc., 90, 223 (1968).

    Google Scholar 

  81. I. S. Kashparov and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 1, 124 (1971).

    Google Scholar 

  82. I. Degani, R. Fochi, and G. Vincenzi, Boll. Sci. Fac. Chim. Ind. Bologna, 23, 21 (1965).

    Google Scholar 

  83. I. H. Pitman and L. A. Sternson, J. Am. Chem. Soc., 98, 5234 (1976).

    Google Scholar 

  84. J. A. Zoltewicz, G. Grahe, and C. L. Smith, J. Am. Chem. Soc., 91, 5501 (1969).

    Google Scholar 

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  1. Rostov State University, 344006, Rostov-on-Don

    A. F. Pozharskii

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1175, September, 1979.

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Pozharskii, A.F. Concept of π-deficiency in the chemistry of heteroaromatic compounds (review). Chem Heterocycl Compd 15, 939–954 (1979). https://doi.org/10.1007/BF00473831

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