Advertisement

Chemistry of Heterocyclic Compounds

, Volume 22, Issue 6, pp 587–608 | Cite as

Effect of the acid-base properties of heteroaromatic compounds on their electrophilic substitution reactions (review)

  • L. I. Belen'kii
Article

Abstract

The effect of the properties of heteroaromatic compounds as acids and bases on their behavior in electrophilic substitution reactions was examined. The established peculiarities were compared with the behavior of functional compounds of the benzene series. The specific characteristics of the mechanisms of electrophilic substitution in the heteroaromatic series due to the acidic and basic properties of the heteroaromatic compounds are discussed.

Keywords

Benzene Organic Chemistry Basic Property Substitution Reaction Electrophilic Substitution 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    L. S. Efros and M. V. Gorelik, The Chemistry and Technology of Intermediates [in Russian], Khimiya, Moscow (1980), Chaps. 1–6.Google Scholar
  2. 2.
    Kh. Khinei, in: General Organic Chemistry [Russian translation], Vol. 1, Khimiya, Moscow (1981), p. 314.Google Scholar
  3. 3.
    A. F. Pozharskii, Theoretical Foundations of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).Google Scholar
  4. 4.
    M. N. Nach and J. F. Bunnett, J. Amer. Chem. Soc.,96, 936 (1974).Google Scholar
  5. 5.
    V. Calo, L. Lopez, G. Pesce, and P. E. Todesco, J. Chem. Soc., Perkin 2, No. 10, 1192 (1974).Google Scholar
  6. 6.
    D. E. Pearson and E. Buehler, Synthesis, No. 5, 455 (1971).Google Scholar
  7. 7.
    V. V. Ershov, G. A. Nikiforov, and A. A. Volod'kin, Sterically Hindered Phenols [in Russian], Khimiya, Moscow (1972).Google Scholar
  8. 8.
    P. F. Ranken and A. G. McKinie, Synthesis, No. 2, 117 (1984).Google Scholar
  9. 9.
    R. C. Cambie, P. S. Rutledge, T. Smith-Palmer, and P. D. Woodgate, J. Chem. Soc., Perkin 1, No. 11, 1161 (1976).Google Scholar
  10. 10.
    Y. Ogata, M. Kimura, Y. Kondo, H. Katoh, and Che-Fa-Ching, J. Chem. Soc., Perkin 2, No. 3, 451 (1984).Google Scholar
  11. 11.
    P. Haberfield and D. Paul, J. Amer. Chem. Soc.,87, 5502 (1965).Google Scholar
  12. 12.
    D. H. Hey, J. A. Leonard, and C. W. Rees, J. Chem. Soc., No. 11, 4579 (1962).Google Scholar
  13. 13.
    A. Guy, M. Lemaire, and J.-P. Guette, Chem. Commun., No. 1, 8 (1980).Google Scholar
  14. 14.
    A. Guy, M. Lemaire, and J.-P. Guette, Tetrahedron,38, 2339 (1982).Google Scholar
  15. 15.
    H. Pervez, L. Rees, and C. J. Suckling, Chem. Commun., No. 8, 512 (1985).Google Scholar
  16. 16.
    B. R. Suthers, P. H. Riggins, and D. E. Pearson, J. Org. Chem.,27, 447 (1962).Google Scholar
  17. 17.
    J. H. Gorvin, J. Chem. Soc., No. 4, 1237 (1953).Google Scholar
  18. 18.
    Organic Syntheses [Russian translation], Vol. 4, Izd. Inostr. Lit., Moscow (1953), p. 374.Google Scholar
  19. 19.
    Z. Vrba and Z. J. Allan, Tetrahedron Lett., No. 43, 4507 (1968).Google Scholar
  20. 20.
    B. M. Lynch, C. M. Chen, and Y. Y. Wigfield, Can. J. Chem.,46, 1141 (1968).Google Scholar
  21. 21.
    P. H. Griffiths, W. A. Walkey, and H. B. Watson, J. Chem. Soc., No. 5, 631 (1934).Google Scholar
  22. 22.
    K. Halvarsson and L. Melander, Arkiv Kemi,11, 77 (1957).Google Scholar
  23. 23.
    R. O. C. Norman and G. H. Radda, J. Chem. Soc., No. 7, 3030 (1961).Google Scholar
  24. 24.
    R. O. C. Norman and G. H. Radda, Proc. Chem. Soc., No. 12, 423 (1960).Google Scholar
  25. 25.
    Organic Syntheses [Russian translation], Vol. 2, Izd. Inostr. Lit., Moscow (1949), p. 116.Google Scholar
  26. 26.
    L. I. Belen'kii, Yu. B. Vol'kenshtein, and I. B. Karmanova, Usp. Khim.,46, 1698 (1977).Google Scholar
  27. 27.
    Organic Syntheses [Russian translation], Vol. 1, Izd. Inostr. Lit., Moscow (1949), p. 475.Google Scholar
  28. 28.
    D. E. Pearson and H. W. Pope, J. Org. Chem., 21, 381 (1956).Google Scholar
  29. 29.
    D. E. Pearson, H. W. Pope, W. N. Hargrowe, and W. E. Stamper, J. Org. Chem.,23, 1412 (1958).Google Scholar
  30. 30.
    L. I. Belen'kii, G. P. Gronova, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 951 (1971).Google Scholar
  31. 31.
    D. H. Derbishire and W. A. Waters, J. Chem. Soc., No. 2, 564 (1950).Google Scholar
  32. 32.
    Ya. L. Gol'dfarb, É. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2822 (1971).Google Scholar
  33. 33.
    Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, Zh. Obshch. Khim.,31. 616 (1961).Google Scholar
  34. 34.
    L. I. Belen'kii, I. B. Karmanova, and Ya. L. Gol'dfarb, Zh. Org. Khim.,9, 1514 (1973).Google Scholar
  35. 35.
    Ya. L. Gol'dfarb, I. B. Karmanova, Yu. B. Vol'kenshtein, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 11, 1474 (1978).Google Scholar
  36. 36.
    J.-P. Gesson, J.-C. Jacquesy, M.-P. Jouannetaud, and G. Morellet, Tetrahedron Lett.,24, 3095 (1983).Google Scholar
  37. 37.
    V. N. Belov, L. A. Kheifits, and S. I. Virezuh, Reactions and Methods for the Investigation of Organic Compounds [in Russian], Book 10, Goskhimizdat, Moscow (1961), p. 7.Google Scholar
  38. 38.
    B. P. Susz and J. Cook, Helv, Chim. Acta,37, 1273 (1954).Google Scholar
  39. 39.
    K. B. Starowiejski, S. Pasynkiewicz, A. Sporzynski, and A. Chowojnowski, J. Organomet. Chem., 94, 361 (1975).Google Scholar
  40. 40.
    L. I. Belen'kii, E. N. Gur'yanova, V. Knoppova, E. D. Lubuzh, I. P. Romm, and R. R. Shifrina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 48 (1980).Google Scholar
  41. 41.
    L. I. Belen'kii, I. B. Karmanova, G. P. Gromova, É. I. Novikova, Ya. L. Gol'dfarb, V. S. Bogdanov, and L. V. Shmelev, Zh. Org. Khim.,9, 1499 (1973).Google Scholar
  42. 42.
    L. I. Belen'kii, V. S. Bogdanov, and I. B. Karmanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1735 (1979).Google Scholar
  43. 43.
    I. P. Romm, L. I. Belen'kii, E. N. Gur'yanova, and Yu. K. Tovbin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2478 (1979).Google Scholar
  44. 44.
    J.-C. Jacquesi, M.-P. Jounnetaud, and S. Makani, Chem. Commun., No. 3, 110 (1980).Google Scholar
  45. 45.
    J. M. Brittain, P. B. D. de la Mare, and P. A. Newman, Tetrahedron Lett., No. 21, 4111 (1980).Google Scholar
  46. 46.
    F. Effenberger and P. Menzel, Angew. Chem.,83, 535 (1971).Google Scholar
  47. 47.
    G. A. Olah, J. A. Olah, and T. Ohyama, J. Amer. Chem. Soc.,106, 5284 (1984).Google Scholar
  48. 48.
    E. Ochiai, J. Pharm. Soc. Japan,60, 164 (1940); Chem. Abstr.,34, 5450 (1940).Google Scholar
  49. 49.
    German Patent No. 433100; Beilstein,26, Suppl. 2, 16 (1954).Google Scholar
  50. 50.
    A. E. A. Porter, in: General Organic Chemistry [Russian translation], Vol. 8, Khimiya, Moscow (1985), p. 190.Google Scholar
  51. 51.
    A. K. Sheinkman, S. I. Suminov, and A. N. Kost, Usp. Khim.,42, 1415 (1973).Google Scholar
  52. 52.
    A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 1, p. 3 (1974).Google Scholar
  53. 53.
    M. Hamana, Khim. Geterotsikl. Soedin., No. 9, 1155 (1973).Google Scholar
  54. 54.
    W. P. K. Girke, Tetrahedron Lett., No. 39, 3537 (1976).Google Scholar
  55. 55.
    W. P. K. Girke, Chem. Ber.,112, 1 (1979).Google Scholar
  56. 56.
    W. P. K. Girke, Chem. Ber.,112. 1348 (1979).Google Scholar
  57. 57.
    A. Kreutzberger, Angew. Chem.,79, 978 (1967).Google Scholar
  58. 58.
    S. V. Krivun, Dokl. Akad. Nauk SSSR,180, 615 (1968).Google Scholar
  59. 59.
    F. Krönnke and K. Dicnore, Chem. Ber.,92. 46 (1959).Google Scholar
  60. 60.
    R. Wizinger and H. Angeliner, Helv. Chim. Acta,49, 2046 (1966).Google Scholar
  61. 61.
    M. P. Carmody, M. J. Cook, N. L. Dassanayake, A. R. Katritzky, P. Linda, and R. D. Tack, Tetrahedron,32, 1767 (1976).Google Scholar
  62. 62.
    Ya. L. Gol'dfarb, E. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6 1233 (1971).Google Scholar
  63. 63.
    A. Albert, in: Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow-Leningrad (1966), pp. 15–124.Google Scholar
  64. 64.
    A. R. Katritzky and C. D. Johnson, Angew. Chem.,79, 629 (1967).Google Scholar
  65. 65.
    S. Clementi, P. P. Forsythe, C. D. Johnson, A. R. Katritzky, and B. Terem, J. Chem. Soc., Perkin 2, No. 4, 399 (1974).Google Scholar
  66. 66.
    A. El-Anani, J. Banger, G. Bianchi, S. Clementi, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin 2, No. 7, 1065 (1973).Google Scholar
  67. 67.
    S. Clementi, P. P. Forsythe, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin 2, No. 12, 1675 (1973).Google Scholar
  68. 68.
    A. R. Katritzky, B. Terem, E. V. Scriver, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin 2, No. 14, 1600 (1975).Google Scholar
  69. 69.
    A. R. Katritzky, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin 2, No. 14, 1624 (1975).Google Scholar
  70. 70.
    A. R. Katritzky, C. Ogretir, H. O. Tarhan, H. M. Dou, and J. V. Metzger, J. Chem. Soc., Perkin 2, No. 14, 1614 (1975).Google Scholar
  71. 71.
    A. R. Katritzky, H. O. Tarhan, and B. Terem, J. Chem. Soc., Perkin 2, No. 14, 1620 (1975).Google Scholar
  72. 72.
    A. R. Katritzky, S. Clementi, G. Milletti, and G. V. Sebastiani, J. Chem. Soc., Perkin 2, No. 6, 613 (1978).Google Scholar
  73. 73.
    D. S. Noyce, J. A. Virgilio, and B. Bartman, J. Org. Chem.,38, 2657 (1973).Google Scholar
  74. 74.
    D. S. Noyce and S. A. Fike, J. Org. Chem.,38, 3316 (1973).Google Scholar
  75. 75.
    D. S. Noyce and G. T. Stowe, J. Org. Chem.,38, 3762 (1973).Google Scholar
  76. 76.
    D. S. Noyce and B. B. Sandel, J. Org. Chem.,40, 3762 (1975).Google Scholar
  77. 77.
    D. S. Noyce and G. V. Kaiser, J. Org. Chem.,34, 1008 (1969).Google Scholar
  78. 78.
    D. S. Noyce and H. J. Pavez, J. Org. Chem.,37, 2620, 2623 (1972).Google Scholar
  79. 79.
    D. S. Noyce, C. A. Lipinski, and R. W. Nichols, J. Org. Chem.,37, 2615 (1972).Google Scholar
  80. 80.
    D. S. Noyce, C. A. Lipinski, and G. M. Loudon, J. Org. Chem.,35, 1718 (1970).Google Scholar
  81. 81.
    D. S. Noyce and B. B. Sandel, J. Org. Chem.,41, 3640 (1976).Google Scholar
  82. 82.
    E. A. Hill, M. L. Gross, M. Stasiewicz, and M. Manion, J. Amer. Chem. Soc.,91, 7381 (1969).Google Scholar
  83. 83.
    T. J. Broxton, G. L. Butt, L. W. Deady, S. H. Toh, R. D. Topsom, A. Fischer, and M. W. Morgan, Can. J. Chem.,51, 1620 (1973).Google Scholar
  84. 84.
    G. T. Bruce, A. R. Cooksey, and K. J. Morgan, J. Chem. Soc., Perkin 2, No. 6, 551 (1975).Google Scholar
  85. 85.
    R. J. Abraham, E. Bullock and S. S. Mitra, Can. J. Chem.,37, 1859 (1959).Google Scholar
  86. 86.
    E. B. Whipple, Y. Chiang, and R. L. Hinman, J. Amer. Chem. Soc.,85, 26 (1963).Google Scholar
  87. 87.
    Y. Chiang and E. B. Whipple, J. Amer. Chem. Soc.,85, 2763 (1963).Google Scholar
  88. 88.
    R. Kassner, E. Krumtholz, and F. W. Stenber, Ann., No. 5, 789 (1981).Google Scholar
  89. 89.
    H. Hogeween, Rec. Trav. Chim.,85, 1072 (1966).Google Scholar
  90. 90.
    H. Hogeween, R. M. Kellogg, and K. A. Kuindersma, Tetrahedron Lett., No. 40, 3929 (1973).Google Scholar
  91. 91.
    L. I. Belen'kii, A. P. Yakubov, and Ya. L. Gol'dfarb, Zh. Org. Khim.,11, 424 (1975).Google Scholar
  92. 92.
    A. P. Yakubov, N. V. Grigor'eva, and L. I. Belen'skii, Zh. Org. Khim., 14, 641 (1978).Google Scholar
  93. 93.
    Ya. L. Gol'dfarb, M. A. Kalik, N. A. Shul'ts, and L. I. Belen'kii, Zh. Org. Khim.,15, 1289 (1979).Google Scholar
  94. 94.
    L. I. Belen'kii and A. P. Yakubov, Tetrahedron,40, 2471 (1984).Google Scholar
  95. 95.
    L. I. Belen'kii and A. P. Yakubov, Tetrahedron,42, 759 (1986).Google Scholar
  96. 96.
    U. E. Wiersum and H. Wynberg, Tetrahedron Lett., No. 31, 2951 (1967).Google Scholar
  97. 97.
    D. M. Brower and J. A. van Doorn, Rec. Trav. Chim.,89. 553 (1970).Google Scholar
  98. 98.
    D. M. Brower, J. A. van Doorn, and A. A. Kiffen, Rec. Trav. Chim.,91, 1359 (1972).Google Scholar
  99. 99.
    V. G. Kul'nevich and Yu. M. Shapiro, Khim. Geterotsikl. Soedin., No. 12, 1594 (1972).Google Scholar
  100. 100.
    L. I. Belen'kii, Khim. Geterotsikl, Soedin., No. 12, 1587 (1980).Google Scholar
  101. 101.
    V. Veinmayr, J. Amer. Chem. Soc.,72, 918 (1950).Google Scholar
  102. 102.
    L. I. Belen'kii, A. P. Yakubov, and I. A. Bessonova, Zh. Org. Khim.,13, 364 (1977).Google Scholar
  103. 103.
    L. I. Belen'kii and N. V. Grigor'eva, in: Topics in the Chemistry of Heterocyclic Compounds, edited by J. Kovac, Bratislava (1981), p. 121.Google Scholar
  104. 104.
    Ya. L. Gol'dfarb, A. A. Dudinov, and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 1323 (1982).Google Scholar
  105. 105.
    Y. Yokoyama, Y. Yamashita, K. Takahashi, and T. Sone, Chem. Lett., No. 6, 813 (1981).Google Scholar
  106. 106.
    Y. Yokoyama, Y. Yamashita, K. Takahashi, and T. Sone, Bull. Chem. Soc. Japan,56, 2208 (1983).Google Scholar
  107. 107.
    Y. Yamashita, A. Yoshino, K. Takahashi, and T. Sone, The 46th National Meeting of the Chemical Society of Japan, Niigata, Oct. 1982, Abstr. 4P15; Y. Yamashita, H. Kobayashi, A. Yoshino, K. Takahashi, and T. Sone, Bull. Chem. Soc. Japan,57, 1312 (1984).Google Scholar
  108. 108.
    G. G. Furin and G. G. Yakobson, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Vol. 1, No. 2, 109 (1977).Google Scholar
  109. 109.
    M. Eckert-Maksic, J. Org. Chem.,45, 3355 (1980).Google Scholar
  110. 110.
    G. V. Boyd and K. Heatherington, J. Chem. Soc., Perkin 1, No. 21, 2523 (1973).Google Scholar
  111. 111.
    C. T. Wie, S. Sunder, and C. D. Bolaniou, Tetrahedron Lett., No. 44, 4605 (1968).Google Scholar
  112. 112.
    G. A. Olah, K. Dunne, D. P. Kelly, and Y. K. Mo, J. Amer. Chem. Soc.,94, 7438 (1972).Google Scholar
  113. 113.
    H. J. Chen, L. E. Hakka, R. L. Hinman, A. J. Kresge, and E. B. Whipple, J, Amer. Chem. Soc.,93, 5102 (1971).Google Scholar
  114. 114.
    T. Yamaoka, H. Hosoya, and S. Nagakura, Tetrahedron,24, 6203 (1968).Google Scholar
  115. 115.
    F. Effenberger and R. Niess, Angew, Chem.,79, 1100 (1967).Google Scholar
  116. 116.
    A. P. Yakubov, L. I. Belen'kii, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 525 (1971).Google Scholar
  117. 117.
    T. A. Melent'eva, T. M. Filippova, L. V. Kazanskaya, I. M. Kustanovich, and V. M. Berezovskii, Zh. Obshch. Khim.,41, 179 (1971).Google Scholar
  118. 118.
    M. I. Struchkova, G. G. Dvoryantseva, N. P. Kostyuchenko, Yu. N. Sheinker, Yu. E. Sklyar, and R. P. Evstigneeva, Khim. Geterotsikl. Soedin., No. 3, 336 (1972).Google Scholar
  119. 119.
    Ya. L. Gol'dfarb, Yu. B. Vol'kenshtein (Volkenstein), and L. I. Belen'kii (Belen'kij), Angew. Chem.,80, 547 (1968).Google Scholar
  120. 120.
    L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 344 (1975).Google Scholar
  121. 121.
    Ya. L. Gol'dfarb (editor), New Directions in the Chemistry of Thiophene [in Russian], Nauka, Moscow (1976).Google Scholar
  122. 122.
    H. J. Anderson and C. E. Loader, Synthesis, No. 4, 353 (1985).Google Scholar
  123. 123.
    L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1228 (1971).Google Scholar
  124. 124.
    Ya. L. Gol'dfarb, G. P. Gromova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2275 (1974).Google Scholar
  125. 125.
    L. I. Belen'kii, Ya. L. Gol'dfarb, and G. P. Gromova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2733 (1973).Google Scholar
  126. 126.
    Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, Dokl. Akad. Nauk SSSR,128, 536 (1959).Google Scholar
  127. 127.
    Ya. L. Gol'dfarb, A. P. Yakubov, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR,185, 941 (1969).Google Scholar
  128. 128.
    L. I. Belen'kii, I. B. Karmanova, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 1743 (1971).Google Scholar
  129. 129.
    L. I. Belen'kii, E. I. Novikova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 9, 1353 (1971).Google Scholar
  130. 130.
    L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 5, 597 (1972).Google Scholar
  131. 131.
    Zh. I. Aksel'rod and V. M. Berezovskii, Usp. Khim.,39, 1337 (1970).Google Scholar
  132. 132.
    H. Saito and M. Hamana, Heterocycles,12, 475 (1979).Google Scholar
  133. 133.
    D. E. Pearson, W. W. Hargrowe, K. T. Judith, and B. R. Suhters, J. Org. Chem.,26, 789 (1961).Google Scholar
  134. 134.
    R. E. Lokhov, S. S. Lokhova, N. M. Gaidarova, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 9, 1236 (1981).Google Scholar
  135. 135.
    H. J. den Hertog, L. van der Does, and C. A. Landheer, Rec. Trav. Chim.,81, 864 (1962).Google Scholar
  136. 136.
    L. van der Does and H. J. den Hertog, Rec. Trav. Chim.,84, 951 (1965).Google Scholar
  137. 137.
    J. Abblard, C. Decoret, L. Cronenberg, and H. Pacheco, Bull. Soc. Chim. France, No. 6, 2466 (1972).Google Scholar
  138. 138.
    E. Gareia, J. Amer. Chem. Soc.,82. 4430 (1960).Google Scholar
  139. 139.
    T. Batkowski, D. Tomasik, and P. Tomasik, Roczn. Chem.,41, 2101 (1967).Google Scholar
  140. 140.
    I. J. Fergusson, M. R. Grimmett, and K. Schofield, Tetrahedron Lett., No. 27, 2771 (1972).Google Scholar
  141. 141.
    J. W. Barnett, I. J. Fergusson, and K. Schofield, unpublished data cited by K. Schofield, M. R. Grimmett, and B. R. T. Keene, in: Heteroatomatic Nitrogen Compounds. The Azoles, Cambridge Univ. Press (1976), p. 68.Google Scholar
  142. 142.
    M. W. Austin, J. R. Blackborow, J. H. Ridd, and B. V. Smith, J. Chem. Soc., No. 2, 1051 (1965).Google Scholar
  143. 143.
    I. I. Grandberg, S. V. Tabak, N. I. Bobrova, A. N. Kost, and L. G. Vasina, Khim. Geterotsikl. Soedin., No. 3, 407 (1965).Google Scholar
  144. 144.
    G. Travagli, Gazz. Chim. Ital.,85, 926 (1955).Google Scholar
  145. 145.
    S. L. Gusinskaya, Khim. Geterotsikl. Soedin., No. 3, 345 (1970).Google Scholar
  146. 146.
    O. P. Shvaika and G. P. Klimisha, Khim. Geterotsikl. Soedin., No. 1, 19 (1966).Google Scholar
  147. 147.
    R. Gompper and H. Ruhle, Ann.,626, 83 (1959).Google Scholar
  148. 148.
    H. S. Suri, G. N. Sharma, and K. S. Narang, J. Indian Chem. Soc.,45, 409 (1968); Chem. Abstr.,69, 77146 (1968).Google Scholar
  149. 149.
    R. Gompper and O. Christman, Chem. Ber.,92, 1944 (1959).Google Scholar
  150. 150.
    L. I. Belen'kii and M. A. Cheskis, Khim. Geterotsikl. Soedin., No. 7, 881 (1984).Google Scholar
  151. 151.
    L. I. Belen'kii, G. P. Gromova, M. A. Cheskis, and Ya. L. Gol'dfarb, Chemica Scripta,25, 295 (1985).Google Scholar
  152. 152.
    M. A. Khan, B. M. Lynch, and Y.-Y. Hung, Can. J. Chem.,41, 1540 (1963).Google Scholar
  153. 153.
    B. M. Lynch and Y.-Y. Hung, Can J. Chem.,42, 1605 (1964).Google Scholar
  154. 154.
    M. R. Grimmett, S. R. Hartshorn, K. Schofield, and J. B. Weston, J. Chem. Soc., Perkin 2, No. 11, 1654 (1972).Google Scholar
  155. 155.
    S. D. Sokolov and I. M. Yudintseva, Zh. Org. Khim.,7, 1765 (1971).Google Scholar
  156. 156.
    R. G. Jones and C. Ainsworth, J. Amer. Chem. Soc.,77, 1538 (1955).Google Scholar
  157. 157.
    R. Hüttel and A. Gebhardt, Ann.,558, 43 (1947).Google Scholar
  158. 158.
    R. Hüttel and G. Welzel, Ann.593. 207 (1955).Google Scholar
  159. 159.
    R. Stolle and F. Henke-Stark, J. Prakt. Chem.,124, 261 (1930).Google Scholar
  160. 160.
    V. P. Karavai and P. N. Gaponik, Khim. Geterotsikl. Soedin., No. 4, 564 (1985).Google Scholar
  161. 161.
    B. M. Lynch, Can. J. Chem.,41, 2380 (1963).Google Scholar
  162. 162.
    B. M. Lynch and T. Chan, Can. J. Chem.,41, 274 (1963).Google Scholar
  163. 163.
    H. El-Khaden, H. A. R. Mansour, and M. H. Meshreki, J. Chem. Soc. (C), No. 11, 1329 (1968).Google Scholar
  164. 164.
    E. Lippmann and A. Könnecke, Z. Chem.,15, 226 (1975).Google Scholar
  165. 165.
    H. W. Gschwend and H. R. Rodriguez, Organic Reactions, Vol. 26, Wiley & Sons, New York (1979), p. 1.Google Scholar
  166. 166.
    R. Hüttel and F. Buehele, Chem. Ber.,88, 1586 (1955).Google Scholar
  167. 167.
    J. W. A. M. Janssen, H. J. Koeners, C. G. Kruse, and C. L. Habraken, J. Org. Chem.,38, 1777 (1973).Google Scholar
  168. 168.
    S. S. Novikov, L. I. Khmel'nitskii, O. V. Lebedev, V. V. Sevast'yanova, and L. V. Epishina, Khim. Geterotsikl. Soedin., No. 4, 503 (1970).Google Scholar
  169. 169.
    R. Miethchen and C.-F. Kroger, Z. Chem.,7, 184 (1967).Google Scholar
  170. 170.
    C.-F. Kroger and H. Frank, Angew. Chem.,77, 425 (1965).Google Scholar
  171. 171.
    C.-F. Kroger and H. Frank, Angew. Chem.,77, 928 (1965).Google Scholar
  172. 172.
    C.-F. Kroger and R. Miethchen, Chem. Ber.,100, 2250 (1967).Google Scholar
  173. 173.
    J. H. Ridd, J. Chem. Soc., No. 4, 1238 (1955).Google Scholar
  174. 174.
    A. Grimison and J. H. Ridd, J. Chem. Soc., Nos. 9/10, 3019 (1959).Google Scholar
  175. 175.
    L. Schutte, P. P. Kluit, and E. Havinga, Tetrahedron, Suppl. No. 7, 295 (1966).Google Scholar
  176. 176.
    R. Breslow, J. Amer. Chem., Soc.,79, 1762 (1957).Google Scholar
  177. 177.
    H. A. Staab, H.-Th. Wu, A. Mannschreck, and G. Schwalbach, Tetrahedron Lett., No. 15, 845 (1964).Google Scholar
  178. 178.
    P. Haake, L. P. Bausher, and W. B. Miller, J. Amer. Chem. Soc.,91, 1113 (1969).Google Scholar
  179. 179.
    J. D. Vaughan, Z. Mughrabi, and E. C. Wu, J. Org. Chem.,35, 1141 (1970).Google Scholar
  180. 180.
    R. A. Coburn, J. M. Landesberg, D. S. Kemp, and R. A. Olofson, Tetrahedron,26, 685 (1970).Google Scholar
  181. 181.
    R. A. Olofson, W. R. Thompson, and J. S. Michelman, J. Amer. Chem. Soc.,86, 1865 (1964).Google Scholar
  182. 182.
    R. A. Olofson and J. M. Landesberg, J. Amer. Chem. Soc.,88, 4263 (1966).Google Scholar
  183. 183.
    E. C. Wu and J. D. Vaughan, J. Org. Chem.,35, 1146 (1970).Google Scholar
  184. 184.
    H. Kohn, S. J. Benkovic, and R. A. Olofson, J. Amer. Chem. Soc.,94, 5759 (1972).Google Scholar
  185. 185.
    E. Regel and K.-H. Buchel, Ann., No. 1, 145 (1977).Google Scholar
  186. 186.
    A. Medici, G. Fantin, M. Fogagnolo, P. Pedrini, A. Dondoni, and G. D. Andreetti, J. Org. Chem.,49, 590 (1984).Google Scholar
  187. 187.
    E. Regel, Ann., No. 1, 159 (1977).Google Scholar
  188. 188.
    R. Fusco, F. D'Ado, and A. Masserini, Gazz. Chim. Ital.,96, 1084 (1966).Google Scholar
  189. 189.
    A. Medici, M. Fogagnolo, P. Pedrini, and A. Dondoni, J. Org. Chem.,47, 3844 (1982).Google Scholar
  190. 190.
    A. Dondoni, G. Fantin, M. Fogagnolo, A. Mastellari, A. Medici, and P. Pedrini, J. Org. Chem.,49, 3478 (1984).Google Scholar
  191. 191.
    E. Anders, H.-G. Boldt, R. Fuchs, and T. Gassner, Tetrahedron Lett.,25, 1715 (1984).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • L. I. Belen'kii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations