Intramolecular Reversible Addition Reactions to the Other Groups

  • Raimonds E. Valters
  • Wilhelm Flitsch
Chapter

Abstract

Numerous synthetic methods for the preparation of heterocyclic imines and amines have been developed [1, 2] in which the last stage involves an intramolecular nucleophilic addition of a hydroxy, amino, or mercapto group to a C≡N bond. Intermediates in these syntheses, i.e., hydroxy, amino, or mercaptonitriles (1A, X = O, NR, S) usually were not isolated.

Keywords

Phosphorus Atom Cyclic Form Tautomeric Equilibrium Thermal Isomerization Cyclic Isomer 
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.
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. I. Meyers and J. C. Sircar, In: The Chemistry of the Cyano Group, Ed. Z. Rappoport, Interscience Publishers, London, 1970, p. 341.CrossRefGoogle Scholar
  2. 2.
    E. N. Zilberman, The Reactions of Nitriles, Khimiya, Moscow, 1972 (In Russian).Google Scholar
  3. 3.
    E. C. Taylor and R. V. Ravindranathan, J. Org. Chem. 1962, 27, 2622.CrossRefGoogle Scholar
  4. 4.
    H. Junek, H. Fischer-Colbrie, H. Aigner, and A. M. Braun, Helv. Chim. Acta 1972, 55, 1459.CrossRefGoogle Scholar
  5. 5.
    R. G. Dubenko and E. F. Gorbenko, Khim. Geterotsikl Soedin. 1967, 923.Google Scholar
  6. 6.
    H. Nohira, Y. Nishikava, Y. Furuya, and T. Mukayama, Bull. Chem. Soc. Jpn. 1965, 38, 897.CrossRefGoogle Scholar
  7. 7.
    R. Kwok and P. Pranc, J. Org. Chem. 1967, 32, 738.CrossRefGoogle Scholar
  8. 8.
    M. Regitz and D. Stadler, Chem. Ber. 1968, 101, 2351.CrossRefGoogle Scholar
  9. 9.
    G. Kille and J.-P. Fleury, Bull. Soc. Chim. Fr. 1967, 4619.Google Scholar
  10. 10.
    J.-P. Fleury and A. Baysang, Bull. Soc. Chim. Fr. 1969, 4102.Google Scholar
  11. 11.
    J.-P. Fleury, A. Baysang, and D. Clerin, Bull. Soc. Chim. Fr. 1969, 4108.Google Scholar
  12. 12.
    S. I. Suminov and A. N. Kost, Zh. Obshch. Khim. 1963, 33, 2208.Google Scholar
  13. 13.
    A. Foucoud, Bull. Soc. Chim. Fr. 1964, 123.Google Scholar
  14. 14.
    E. C. Taylor and R. W. Hendess, J. Am. Chem. Soc. 1965, 87, 1995.CrossRefGoogle Scholar
  15. 15.
    J. Le Ludec, D. Danion, and R. Carrie, Bull. Soc. Chim. Fr. 1966, 3895.Google Scholar
  16. 16.
    T. L. Patton, J. Org. Chem. 1967, 32, 383.CrossRefGoogle Scholar
  17. 17.
    E. C. Taylor, A. McKillop, Y. Shvo, and G. H. Havks, Tetrahedron 1967, 23, 2081.CrossRefGoogle Scholar
  18. 18.
    Z. Höhn, Z. Chem. 1970, 10, 386.CrossRefGoogle Scholar
  19. 19.
    W. Klötzner, R. Franzmair, and H. Bretschneider, Monatsh. Chem. 1970, 101, 1263.CrossRefGoogle Scholar
  20. 20.
    J. N. Wells, W. J. Wheeler, and L. M. Davisson, J. Org. Chem. 1971, 36, 1503.CrossRefGoogle Scholar
  21. 21.
    T. S. Safonova, M. P. Nemeryuck, L. A. Mishkina, and N. I. Traven’, Khim. Geterotsikl. Soedin. 1972, 944.Google Scholar
  22. 22.
    R. E. Valters, A. E. Bace, and S. P. Valtere, Law. PSR Zinat. Akad. Vestis, Kim. Ser. 1972, 726.Google Scholar
  23. 23.
    V. Szabo, J. Borda, and E. Theisz, Acta Chim. Acad. Sci. Hung. 1980, 103, 271.Google Scholar
  24. 24.
    G. Cignarella and U. Teotino, J. Am. Chem. Soc. 1960, 82, 1594.CrossRefGoogle Scholar
  25. 25.
    D. E. Balode, R. E. Valters, and S. P. Valtere, Khim. Geterotsikl. Soedin. 1978, 1632;Google Scholar
  26. 25a.
    see also R. E. Valters, R. B. Kampare, S. P. Valtere, D. E. Balode, and A. E. Bace, Khim. Geterotsikl. Soedin. 1983, 1635.Google Scholar
  27. 26.
    R. E. Valters and S. P. Valtere, Khim. Geterotsikl. Soedin. 1972, 281.Google Scholar
  28. 27.
    A. Braun and J. Tcherniac, Ber. Dtsch. Chem. Ges. 1907, 40, 2709.CrossRefGoogle Scholar
  29. 28.
    H. Matsui and S. Ishimoto, Tetrahedron Lett. 1966, 1827.Google Scholar
  30. 29.
    M. Renson and R. Colienne, Bull. Soc. Chim. Belg. 1964, 73, 491.CrossRefGoogle Scholar
  31. 30.
    H. des Abbayes, Bull. Soc. Chim. Fr. 1970, 3661.Google Scholar
  32. 31.
    G. Pangdon, G. Thuillier, and P. Rumpf, Bull. Soc. Chim. Fr. 1970, 1991.Google Scholar
  33. 32.
    E. C. Taylor and P. K. Loeffler, J. Am. Chem. Soc. 1960, 82, 3147.CrossRefGoogle Scholar
  34. 33.
    J. A. Settepani and A. B. Borkovec, J. Heterocycl. Chem. 1966, 3, 188.Google Scholar
  35. 34.
    F. S. Babichev and A. K. Tiltin, Ukr. Khim. Zh. 1970, 36, 62.Google Scholar
  36. 35.
    J. T. Shaw, D. M. Taylor, F. J. Corbett, and J. D. Ballentine, J. Heterocycl Chem. 1972, 9, 125.CrossRefGoogle Scholar
  37. 36.
    G. Coispeau and J. Elguero, Bull. Soc. Chim. Fr. 1970, 2717.Google Scholar
  38. 37.
    P. E. Gagnon, J. L. Boiwin, and R. N. Jones, Can. J. Res. 1949, 27B, 190.CrossRefGoogle Scholar
  39. 38.
    P. E. Gagnon, J. L. Boiwin, P. A. Boiwin, and R. N. Jones, Can. J. Chem. 1951, 29, 182.CrossRefGoogle Scholar
  40. 39.
    P. E. Gagnon, J. L. Boiwin, and A. Chisholm, Can. J. Chem. 1952, 30, 904.CrossRefGoogle Scholar
  41. 40.
    R. E. Valters, E. A. Baumanis, L. K. Stradina, and E. E. Liepins, Khim. Geterotsikl. Soedin. 1981, 516.Google Scholar
  42. 41.
    J. Eby and J. A. Moore, J. Org. Chem. 1967, 32, 1346.CrossRefGoogle Scholar
  43. 42.
    S. G. Tadevosyan, E. N. Teleshov, I. V. Vasil’eva, and A. N. Pravednikov, Zh. Org. Khim. 1980, 16, 353.Google Scholar
  44. 43.
    A. R. Butler, J. Chem. Soc. Perkin Trans. 2 1974, 1239.Google Scholar
  45. 44.
    J. Zabicky, Chem. Ind. 1964, 236.Google Scholar
  46. 45.
    I. V. Vasil’eva, S. G. Tadevosyan, E. N. Teleshov, and A. N. Pravednikov, Dokl. Akad. Nauk SSSR 1981, 256, 398.Google Scholar
  47. 46.
    M. St. C. Flett, Spectrochim. Acta 1962, 18, 1537.Google Scholar
  48. 47.
    L. J. Bellamy, Advances in Infrared Group Frequencies, Methuen and Co., Ltd., Bungay, 1968, Chapter 5 and 8.Google Scholar
  49. 48.
    M. E. Baguley and J. A. Elvidge, J. Chem. Soc. 1957, 709.Google Scholar
  50. 49.
    K. W. Breukink and P. E. Verkade, Rec. Trav. Chim. 1960, 79, 443.CrossRefGoogle Scholar
  51. 50.
    G. W. Stacy, A. J. Papa, F. W. Villaescusa, and S. C. Ray, J. Org. Chem. 1964, 29, 607.CrossRefGoogle Scholar
  52. 51.
    G. W. Stacy, F. W. Willaescusa, and T. E. Wollner, J. Org. Chem. 1965, 30, 4074.CrossRefGoogle Scholar
  53. 52.
    G. W. Stacy and T. E. Wollner, J. Org. Chem. 1967, 32, 3028.CrossRefGoogle Scholar
  54. 53.
    D. L. Eck and G. W. Stacy, J. Heterocycl. Chem. 1969, 6, 147.CrossRefGoogle Scholar
  55. 54.
    G. Simchen and G. Entenmann, Angev. Chem. 1973, 85, 155.CrossRefGoogle Scholar
  56. 55.
    G. Simchen and M. Häfner, Justus Liebigs Ann. Chem. 1974, 1802.Google Scholar
  57. 56.
    G. Simchen and G. Entenmann, Justus Liebigs Ann. Chem. 1977, 1249.Google Scholar
  58. 57.
    P. R. Jones, Chem. Rev. 1963, 63, 461.CrossRefGoogle Scholar
  59. 58.
    T. I. Temnikova, The Course of Theoretical Principles of Organic Chemistry, Khimiya, Leningrad, 1968, Chapter 26 (In Russian)Google Scholar
  60. 58a.
    I. N. Nazarov, Uspekhi Khimii, 1951 20, 71 and 309.Google Scholar
  61. 59.
    V. I. Staninets and E. A. Shilov, Uspekhi Khimii 1971, 40, 491; Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin. 1982, 1443.Google Scholar
  62. 60.
    A. Lattes, Khim. Geterotsikl. Soedin. 1975, 7.Google Scholar
  63. 61.
    M. D. Dowle and D. I. Dawies, Chem. Soc. Rev. 1979, 8, 171.CrossRefGoogle Scholar
  64. 62.
    T. Teitei, Aust. J. Chem. 1982, 35, 1231.CrossRefGoogle Scholar
  65. 63.
    E. Napolitano, R. Fiaschi, and A. Marsili, Tetrahedron Lett. 1983, 24, 1319.CrossRefGoogle Scholar
  66. 64.
    L. R. Letsinger, E. N. Oftedahl, and I. R. Nazy, J. Am. Chem. Soc. 1965, 87, 742.CrossRefGoogle Scholar
  67. 65.
    R. P. Linstead and H. N. Rydon, J. Chem. Soc. 1933, 580.Google Scholar
  68. 66.
    B. D. Whelton and A. C. Huitric, J Org. Chem. 1970, 35, 3143.CrossRefGoogle Scholar
  69. 67.
    T. Hashimoto and S. Nagase, J. Pharm. Soc. Jpn. 1960, 80, 1637.Google Scholar
  70. 68.
    H. H. Baer and L. Urbas, In: The Chemistry of the Nitro and Nitroso Groups, Ed. H. Feuer, Interscience Publishers, New York, 1970, Vol. 2, Chapter 3.Google Scholar
  71. 69.
    H. H. Baer and F. Kienzle, Can. J. Chem. 1965, 43, 190.CrossRefGoogle Scholar
  72. 70.
    R. T. Borchardt and L. A. Cohen, J. Am. Chem. Soc. 1972, 94, 9175.CrossRefGoogle Scholar
  73. 71.
    G. Pitacco and V. Ennio, Tetrahedron Lett. 1978, 2339.Google Scholar
  74. 72.
    S. Chimichi, R. Nesi, M. Scotton, C. Mannucci, and G. Adembri, J. Chem. Soc. Perkin Trans. 2, 1980, 1339Google Scholar
  75. 72a.
    See also S. Chimichi, R. Nesi, F. De Sio, R. Pepino, and A. Degl’Innocenti, Gazz. Chim. Ital. 1982, 112, 249Google Scholar
  76. 72b.
    R. Nesi, S. Chimichi, F. De Sio, and M. Scotton, Org. Magn. Reson. 1983, 21, 42.CrossRefGoogle Scholar
  77. 73.
    E. A. Hill, J. Organomet. Chem. 1975, 91, 123.CrossRefGoogle Scholar
  78. 74.
    E. A. Hill, Adv. Organomet. Chem. 1977, 16, 131.CrossRefGoogle Scholar
  79. 75.
    E. A. Hill and M. M. Myers, J. Organomet. Chem. 1979, 173, 1.CrossRefGoogle Scholar
  80. 76.
    E. A. Hill, D. C. Link, and P. Donndelinger, J. Org. Chem. 1981, 46, 1177.CrossRefGoogle Scholar
  81. 77.
    E. A. Hill and H. R. Ni, J. Org. Chem. 1971, 36, 4133.CrossRefGoogle Scholar
  82. 78.
    F. H. Westheimer, Acc. Chem. Res. 1969, 1, 70.CrossRefGoogle Scholar
  83. 79.
    R. F. Hudson and C. Brown, Acc. Chem. Res. 1972, 5, 204.CrossRefGoogle Scholar
  84. 80.
    S. J. Benkovic and K. J. Schray, In: Transition States in Biochemical Processes, Ed. R. D. Gandour and R. L. Schowen, Plenum, New York, 1978, p. 493.Google Scholar
  85. 81.
    E. E. Nifant’ev and L. M. Matveeva, Zh. Obshch. Khim. 1969, 39, 1555.Google Scholar
  86. 82.
    B. A. Arbuzov and N. A. Polezhaeva, Uspekhi Khimii 1974, 43, 933.Google Scholar
  87. 83.
    F. Ramirez, M. Nowakovski, and J. F. Marecek, J. Am. Chem. Soc. 1976, 98, 4330.CrossRefGoogle Scholar
  88. 84.
    A. Munoz, M. Galagher, R. Klaebe, and R. Wolf, Tetrahedron Lett. 1976, 673.Google Scholar
  89. 85.
    G. Kemp and S. Trippett, Tetrahedron Lett. 1976, 4381.Google Scholar
  90. 86.
    F. Ramirez, M. Nowakovski, and J. F. Marecek, J. Am. Chem. Soc. 1977, 99, 4515.CrossRefGoogle Scholar
  91. 87.
    R. Sarma, F. Ramirez, B. McKeever, M. Nowakovski, and J. F. Marecek, J. Am. Chem. Soc. 1978, 100, 5391.CrossRefGoogle Scholar
  92. 88.
    G. Kemp and S. Trippett, J. Chem. Soc. Perkin Trans 1 1979, 879.CrossRefGoogle Scholar
  93. 89.
    Ch. Bui-Cong, A. Munoz, M. Sanchez, and A. Klaebe, Tetrahedron Lett. 1977, 1587.Google Scholar
  94. 90.
    A. Munoz, B. Garrigues, and M. Koenig, J. Chem. Soc. Chem. Commun. 1978, 219.Google Scholar
  95. 91.
    A. Munoz, B. Garrigues, and M. Koenig, Tetrahedron 1980, 36, 2647.CrossRefGoogle Scholar
  96. 92.
    I. Granoth and J. C. Martin, J. Am. Chem. Soc. 1978, 100, 5229.CrossRefGoogle Scholar
  97. 93.
    I. Granoth and J. C. Martin, J. Am. Chem. Soc. 1979, 101, 4618.CrossRefGoogle Scholar
  98. 94.
    Y. Segall and I. Granoth, J. Am. Chem. Soc. 1979, 101, 3687.CrossRefGoogle Scholar
  99. 95.
    I. Granoth, R. Alkabets, and E. Shirin, J. Chem. Soc. Chem. Commun. 1981, 981.Google Scholar
  100. 96.
    I. Granoth, R. Alkabets, and Y. Segall, J. Chem. Soc. Chem. Commun. 1981, 622.Google Scholar
  101. 97.
    S. J. Benkovic, Compr. Chem. Kinetics 1969, 10, 1.CrossRefGoogle Scholar
  102. 98.
    J. C. Martin and E. F. Perozzi, Science 1976, 191, 154.CrossRefGoogle Scholar
  103. 99.
    A. Munoz, Bull. Soc. Chim. Fr. 1977, 728.Google Scholar
  104. 100.
    H. B. Stegmann, G. Bauer, E. Breitmaier, E. Herrmann, and K. Scheffler, Phosphorus 1975, 5, 207.Google Scholar
  105. 101.
    H. B. Stegmann, R. Haller, and K. Scheffler, Chem. Ber. 1977, 110, 3817.CrossRefGoogle Scholar
  106. 102.
    H. B. Stegmann, R. Haller, A. Burmester, and K. Scheffler, Chem. Ber. 1981, 114, 14.CrossRefGoogle Scholar
  107. 103.
    H. B. Stegmann, H. V. Dumm, and K. B. Ulmschneider, Tetrahedron Lett. 1976, 2007.Google Scholar
  108. 104.
    H. B. Stegmann, H. Müller, K. B. Ulmschneider, and K. Scheffler, Chem. Ber. 1979, 112, 2444.CrossRefGoogle Scholar
  109. 105.
    J. C. Martin and E. F. Perozzi, J. Am. Chem. Soc. 1974, 96, 3155.CrossRefGoogle Scholar
  110. 106.
    T. M. Balthazor and J. C. Martin, J. Am. Chem. Soc. 1975, 97, 5634.CrossRefGoogle Scholar
  111. 107.
    P. Livant and J. C. Martin, J. Am. Chem. Soc. 1977, 99, 5761.CrossRefGoogle Scholar
  112. 108.
    B. Dahlen, Acta Crystallograph. 1973, B29, 595.CrossRefGoogle Scholar
  113. 109.
    P. Livant and J. C. Martin, J. Am. Chem. Soc. 1976, 98, 7851.CrossRefGoogle Scholar
  114. 110.
    W. Nakanishi, S. Murata, Y. Ikeda, T. Sugawara, Y. Kawada, and H. Iwamura, Tetrahedron Lett. 1981, 22, 4241. CrossRefGoogle Scholar
  115. 111.
    W. Nakanishi, Y. Ikeda, and H. Iwamura, J. Org. Chem. 1982, 47, 2275.CrossRefGoogle Scholar
  116. 112.
    W. Nakanishi, S. Matsumoto, Y. Ikeda, T. Sugawara, Y. Kawada, and H. Iwamura, Chem. Letters 1981, 1353.Google Scholar
  117. 113.
    R. Bell and K. J. Morgan, J. Chem. Soc. 1960, 1209.Google Scholar
  118. 114.
    G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc. 1965, 3721.Google Scholar
  119. 115.
    W. Wolf and L. Steinberger, J. Chem. Soc. Chem. Commun. 1965, 449.Google Scholar
  120. 116.
    H. Siebert and M. Handrich, Z. anorg. und allgem. Chem. 1976, 426, 173.CrossRefGoogle Scholar
  121. 117.
    H. J. Barber and M. A. Henderson, J. Chem. Soc. Sect. C 1970, 862.Google Scholar
  122. 118.
    J. Z. Gougoutas and J. C. Clardy, J. Solid State Chem. 1972, 4, 226.CrossRefGoogle Scholar
  123. 119.
    H. Jaffe and J. E. Leffler, J. Org. Chem. 1975, 40, 797.CrossRefGoogle Scholar
  124. 120.
    T. M. Balthazor, J. A. Miles, and B. R. Stults, J. Org. Chem. 1978, 43, 4538.CrossRefGoogle Scholar
  125. 121.
    J. E. Leffler, L. K. Dyall, and P. W. Inward, J. Am. Chem. Soc. 1963, 85, 3443.CrossRefGoogle Scholar
  126. 122.
    J. E. Leffler and H. Jaffe, J. Org. Chem. 1973, 38, 2719.CrossRefGoogle Scholar
  127. 123.
    R. L. Amey and J. C. Martin, J. Org. Chem. 1979, 44, 1779.CrossRefGoogle Scholar
  128. 124.
    L. J. Andrews and R. M. Keefer, J. Am. Chem. Soc. 1959, 81, 2374.CrossRefGoogle Scholar
  129. 125.
    T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem. 1979, 44, 1447.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1985

Authors and Affiliations

  • Raimonds E. Valters
    • 1
  • Wilhelm Flitsch
    • 2
  1. 1.Faculty of ChemistryA. Pelshe Riga Polytechnical InstituteRigaUSSR
  2. 2.Organisch-Chemisches InstitutWestfälischen Wilhelms-UniversitätMünsterFederal Republic of Germany

Personalised recommendations