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Nucleophilic reactions involving opening and closing of saturated heterorings (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Experimental and calculated data on the mechanism and principal kinetic characteristics of processes involving the opening of saturated heterorings by nucleophiles, as well as reactions involving ring closing that proceed with departure of a nucleophilic particle, are correlated.

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Literature Cited

  1. G. A. Olah, Halonium Ions, Wiley-Interscience, New York (1975), p. 15.

    Google Scholar 

  2. D. Barton and U. D. Ollis (eds.), General Organic Chemistry [Russian translation], Vol. 5, Khimiya, Moscow (1983).

    Google Scholar 

  3. B. Capon and S. P. McManus, Neighboring Group Participation, Vol. 1, Plenum Press, New York (1976), p. 3.

    Google Scholar 

  4. X.-K. Jiang, W.-R, Fan, and Y.-Z, Hui, J. Am. Chem. Soc., 106, 7202 (1984).

    Google Scholar 

  5. A. F. Pozharskii, Theoretical Foundations of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).

    Google Scholar 

  6. O. C. Dermer and G. E. Ham, Ethyleneimine and Other Aziridines, Academic Press, New York (1969).

    Google Scholar 

  7. Ya. F. Freimanis (ed.), Order of the Workers' Red Banner Institute of Organic Synthesis. 1957–1981 [in Russian], Zinatne, Riga (1982), p. 19.

    Google Scholar 

  8. A. Hassner (ed.), The Chemistry of Heterocyclic Compounds, Vol. 42, Part 1, Wiley-Interscience, New York (1983).

    Google Scholar 

  9. L. Ruzicka, W. Brugger, M. Pfeiffer, H. Schinz, and M. Stoll, Helv. Chim. Acta, 9, 499 (1926).

    Google Scholar 

  10. C. J. M. Stirling, Israel J. Chem., 21, 111 (1981).

    Google Scholar 

  11. C. J. M. Stirling, Pure Appl. Chem., 56, 1781 (1984).

    Google Scholar 

  12. A. A. Akhrem, A. M. Moiseenkov, and V. N. Dobrynin, Usp. Khim., 37, 1025 (1968).

    Google Scholar 

  13. J. G. Buchanan and H. Z. Sable, Selective Organic Transformations, edited by B. S. Thyagarajan, Vol. 1, Wiley-Interscience, New York (1972), p. 1.

    Google Scholar 

  14. T. J. Mason, Special Periodical Reports. Heterocycl. Chem., 5, 1 (1986).

    Google Scholar 

  15. A. V. Fokin and A. F. Kolomiets, The Chemistry of Thiiranes [in Russian], Nauka, Moscow (1978).

    Google Scholar 

  16. P. E. Peterson, Acc. Chem. Res., 4, 407 (1971).

    Google Scholar 

  17. J. E. Baldwin and M. J. Lusch, Tetrahedron, 38, 2939 (1982).

    Google Scholar 

  18. V. R. Gaertner, J. Heterocycl. Chem., 8., 177 (1971).

    Google Scholar 

  19. J. F. Bunnett, R. L. McDonald, and F. P. Olsen, J. Am. Chem. Soc., 96, 2855 (1974).

    Google Scholar 

  20. H. Stamm, P. Assithianakis, B. Bucholz, and R. Weiss, Tetrahedron Lett., 40, 3571 (1982).

    Google Scholar 

  21. D. J. Goldsmith, E. Kennedy, and R. G. Campbell, J. Org. Chem., 40, 3571 (1975).

    Google Scholar 

  22. M. J. S. Dewar and G. P. Ford, J. Am. Chem. Soc., 101, 783 (1979).

    Google Scholar 

  23. K. J. Ivin and T. Saegusa (eds.), Ring-Opening Polymerization, Vol. 2, Elsevier, London (1984).

    Google Scholar 

  24. T. N. Wade, J. Org. Chem., 45, 5328 (1980).

    Google Scholar 

  25. A. M. Ross, T. M. Pohl, K. Piazza, M. Thomas, B. Fox, and D. L. Whalen, J. Am. Chem. Soc., 104, 1658 (1982).

    Google Scholar 

  26. D. Durham and C. A. Kingsbery, J. Chem. Soc., Perkin 2, No. 7, 923 (1986).

    Google Scholar 

  27. L. M. Timofeeva and V. G. Avakyan, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1557 (1980).

    Google Scholar 

  28. S. G. Koldobskii, V. A. Bobylev, G. F. Tereshchenko, and Yu. V. Puzanov, Zh. Obshch. Khim., 53, 2356 (1983).

    Google Scholar 

  29. S. G. Koldobskii, G. F. Tereshchenko, V. A. Bobylev, and A. R. Dalin, Khim. Geterotsikl. Soedin., No. 8, 1042 (1986).

    Google Scholar 

  30. V. Ross, Advances in the Study of Cancer [Russian translation], Vol. 1, Inostr. Lit., Moscow (1955), p. 511.

    Google Scholar 

  31. S. Ikegami, K. Uoji, and S. Akaboshi, Tetrahedron, 30, 2077 (1974).

    Google Scholar 

  32. W. H. Richardson, C. M. Golina, R. H. Wachs, and M. B. Yelvington, J. Org. Chem., 36, 943 (1971).

    Google Scholar 

  33. C. J. M. Stirling, J. Chem. Educ., 50, 844 (1973).

    Google Scholar 

  34. A. C. Knipe, J. Chem. Soc., Perkin 2, No. 5, 589 (1973).

    Google Scholar 

  35. R. Bird, A. C. Knipe, and C. J. M. Stirling, J. Chem. Soc., Perkin 2, No. 9, 1215 (1973).

    Google Scholar 

  36. T. H. Cromartie and C. G. Swain, J. Am. Chem. Soc., 97, 232 (1975).

    Google Scholar 

  37. G. Illuminati, L. Mandolini, and B. Masci, J. Am. Chem. Soc., 97, 4960 (1975).

    Google Scholar 

  38. T. H. Cromartie and C. G. Swain, J. Am. Chem. Soc., 98, 545 (1976).

    Google Scholar 

  39. C. Galli, G. Illuminati, L. Mandolini, and P. Tamborra, J. Am. Chem. Soc., 99, 2591 (1977).

    Google Scholar 

  40. G. Illuminati, L. Mandolini, and B. Masci, J. Am. Chem. Soc., 99, 6308 (1977).

    Google Scholar 

  41. G. Gondos, K. L. Lang, A. Szeghy, G. Donali, and G. Bernath, J. Chem. Soc., Perkin 1, No. 7, 1770 (1979).

    Google Scholar 

  42. G. Illuminati and L. Mandolini, Acc Chem. Res., 14, 95 (1981).

    Google Scholar 

  43. N. Yahiro, Chem. Lett., No. 9, 1479 (1982).

    Google Scholar 

  44. J. O. Knipe, P. J. Vasquez, and J. K. Coward, J. Am. Chem. Soc., 104, 3202 (1982).

    Google Scholar 

  45. R. Bird, G. Griffiths, G. F. Griffiths, and C. J. M. Stirling, J. Chem. Soc., Perkin 2, No. 5, 579 (1982).

    Google Scholar 

  46. F. Benedetti and C. J. M. Stirling, Chem. Commun., No. 22, 1374 (1983).

    Google Scholar 

  47. M. A. Casadei, C. Galli, and L. Mandolini, J. Am. Chem. Soc., 106, 1051 (1984).

    Google Scholar 

  48. S. P. McManus, N. Neamati-Mazrach, B. A. Honanes, M. S. Palcy, and J. M. Harris, J. Am. Chem. Soc., 107, 3393 (1985).

    Google Scholar 

  49. A. D. Martino, C. Galli, P. Gargano, and L. Mandolini, J. Chem. Soc., Perkin 2, No. 9, 1345 (1985).

    Google Scholar 

  50. Y.-C. Yang, J. R. Ward, and T. Luteran, J. Org. Chem., 51, 2756 (1986).

    Google Scholar 

  51. J. Malek and P. Silhavy, Coll. Czech. Chem. Commun., 41, 84 (1976).

    Google Scholar 

  52. H. El Meslohi and C. Petrus, Bull. Soc. Chim. France, No. 1, 37 (1982).

    Google Scholar 

  53. S. Szakacs, S. Gobolos, and F. Nagy, J. Chem. Soc., Perkin 2, No. 4, 417 (1983).

    Google Scholar 

  54. S. S. Khripko, Zh. Org. Khim., 22, 50 (1986).

    Google Scholar 

  55. E. J. Goethals, E. H. Schacht, Y. E. Bogaert, I. Alis, and Y. Tezuka, Polym. J., 12, 571 (1980).

    Google Scholar 

  56. G. Cerichelli, G. Illuminati, and C. Lillocci, J. Org. Chem., 45, 3952 (1980).

    Google Scholar 

  57. G. Cospito, G. Illuminati, C. Lillocci, and H. Perride, J. Org. Chem., 46, 2944 (1981).

    Google Scholar 

  58. P. Ya. Palutaa, U. V. Soomet-s, and Ya. L. Yarv, Reakts. Sposobnost' Org. Soedin., 22, 236 (1985).

    Google Scholar 

  59. V. S. Borisenko, V. A. Bobylev, S. G. Koldobskii, and G. F. Tereshchenko, Zh. Obshch. Khim., 56, 2768 (1986).

    Google Scholar 

  60. A. R. Dalin, V. A. Bobylev, V. F. Suslikov, S. G. Koldobskii, and G. F. Tereshchenko, Zh. Obshch. Khim., 56, 2774 (1986).

    Google Scholar 

  61. A. Yu. Shibaev, N. V. Astrat'eva, and G. F. Tereshchenko, Zh. Obshch. Khim., 54, 2744 (1984).

    Google Scholar 

  62. G. Alagona, E. Scrocco, and J. Tomasi, Theor. Chim. Acta, 51, 11 (1979).

    Google Scholar 

  63. G. Berti, B. Macchia, and F. Macchia, Tetrahedron, 28, 1299 (1972).

    Google Scholar 

  64. I. P. Beletskaya, Usp. Khim., 44, 2205 (1975).

    Google Scholar 

  65. V. S. Borisenko, V. A. Bobylev, and G. F. Tereshchenko, Zh. Obshch. Khim., 55, 1141 (1985).

    Google Scholar 

  66. S. G. Koldobskii, V. A. Bobylev, G. F. Tereshchenko, A. R. Dalin, and B. V. Gidaspov, Dokl. Akad. Nauk SSSR, 293, 112 (1987).

    Google Scholar 

  67. J. F. Liebman and A. Greenber, Chem. Rev., 76, 311 (1976).

    Google Scholar 

  68. M. Kh. Karapet'yants and M. L. Karapet'yants, Principal Thermodynamic Constants of Inorganic and Organic Substances [in Russian], Khimiya, Moscow (1968).

    Google Scholar 

  69. U. Burkert and N. Allinger, Molecular Mechanics [Russian translation], Mir, Moscow (1986).

    Google Scholar 

  70. V. H. Wysocki, D. J. Burinsky, and R. G. Cooks, J. Org. Chem., 50, 1287 (1985).

    Google Scholar 

  71. O. I. Asubiojo and J. I. Brauman, J. Am. Chem. Soc., 101, 3715 (1979).

    Google Scholar 

  72. I. I. Mutin, Kh. A. Arutyunyan, S. P. Davtyan, and B. A. Rozenberg, Kinet. Katal., 20, 1567 (1979).

    Google Scholar 

  73. O. A. Mislyuk, V. I. Shibaev, and K. A. V'yunov, Zh. Org. Khim., 22, 2502 (1986).

    Google Scholar 

  74. S. G. Koldobskii, G. F. Tereshchenko, V. A. Bobylev, and A. R. Dalin, Khim. Geterotsikl. Soedin., No. 8. 1036 (1986).

    Google Scholar 

  75. M. L. Di Vona, G. Illuminati, and C. Lillocci, J. Chem. Soc., Perkin 2, No. 9, 1943 (1985).

    Google Scholar 

  76. P. Costantino, P. Crotti, M. Ferretti, and E. Mastrorilli, J. Org. Chem., 47., 2917 (1982).

    Google Scholar 

  77. P. Crotti, M. Ferreti, F. Macchia, and A. Stoppioni, J. Org. Chem., 51., 2759 (1986).

    Google Scholar 

  78. G. Berti, S. Canedoli, P. Crotti, and F. Macchia, J. Chem. Soc., Perkin 1, No. 9, 1183 (1984).

    Google Scholar 

  79. M. V. Bazilevskii, S. G. Koldobskii, and V. A. Tikhomirov, Usp. Khim., 55, 1667 (1986).

    Google Scholar 

  80. C. K. Ingold, Theoretical Foundations of Organic Chemistry [Russian translation], Mir, Moscow (1973), p. 391.

    Google Scholar 

  81. G. Cerichelli, C. Galli, C. Lillocci, and L. Luchetti, J. Chem. Soc., Perkin 2, No. 5, 725 (1985).

    Google Scholar 

  82. C. A. Coulson and W. E. Moffitt, Philos. Mag., 40, 1 (1949).

    Google Scholar 

  83. A. D. Walsh, Trans. Faraday Soc., 45, 179 (1949).

    Google Scholar 

  84. M. J. S. Dewar, J. Am. Chem. Soc., 106, 669 (1984).

    Google Scholar 

  85. M. N. Glukhovtsev, B. Ya. Simkin, and V. I. Minkin, Zh. Org. Khim., 22, 3 (1986).

    Google Scholar 

  86. D. Cremer and J. Gauss, J. Am. Chem. Soc., 108, 7467 (1986).

    Google Scholar 

  87. D. Cremer and E. Kraka, J. Am. Chem. Soc., 107, 3800 (1985).

    Google Scholar 

  88. R. F. W. Bader, T. S. Slee, D. Cremer, and E. Kraka, J. Am. Chem. Soc., 105, 5061 (1983).

    Google Scholar 

  89. M. Speranza and G. Angelini, J. Am. Chem. Soc., 102, 3115 (1980).

    Google Scholar 

  90. M. Inone, Y. Taguchi, T. Sugita, and K. Ichikawa, Bull. Chem. Soc Jpn., 51, 2098 (1978).

    Google Scholar 

  91. O. Kikuchi, A. J. Hopfinger, and G. Klopman, Biopolymers, 19, 325 (1980).

    Google Scholar 

  92. G. Lamaty, R. Maleq, C. Selve, A. Sivade, and J. Wylde, J. Chem. Soc., Perkin 2, No. 10, 1119 (1975).

    Google Scholar 

  93. H. Stamm, A. Sommer, A. Woderer, T. Wiesent, T. Mall, and P. Assithianakis, J. Org. Chem., 50, 4946 (1985).

    Google Scholar 

  94. A. V. Willi, Helv. Chim. Acta, 56, 2094 (1973).

    Google Scholar 

  95. D. F. De Tar and N. P. Luthra, J. Am. Chem. Soc., 102, 4505 (1980).

    Google Scholar 

  96. L. M. Timofeeva and D. S. Zhuk, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 442 (1984).

    Google Scholar 

  97. S. M. Van der Kerk, J. W. Verhoeven, and C. J. M. Stirling, J. Chem. Soc., Perkin 2, No. 9, 1355 (1985).

    Google Scholar 

  98. S. Hughes and C. J. M. Stirling, Chem. Commun., No. 4, 237 (1982).

    Google Scholar 

  99. H. A. Earl, D. R. Marshall, and C. J. M. Stirling, Chem. Commun., No. 14, 779 (1983).

    Google Scholar 

  100. G. B. Payne, J. Org. Chem., 27, 3819 (1962).

    Google Scholar 

  101. C. H. Behrens, S. Y. Ko, K. B. Sharpless, and F. J. Walker, J. Org. Chem., 50, 5687 (1985).

    Google Scholar 

  102. R. W. Strozieer, P. Caramella, and K. N. Houk, J. Am. Chem. Soc., 101, 1340 (1979).

    Google Scholar 

  103. S. Nagase and K. Morokuma, J. Am. Chem. Soc., 100, 1666 (1978).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1168, September, 1988.

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Bobylev, V.A., Koldobskii, S.G., Tereshchenko, G.F. et al. Nucleophilic reactions involving opening and closing of saturated heterorings (review). Chem Heterocycl Compd 24, 947–959 (1988). https://doi.org/10.1007/BF00474036

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