Skip to main content
SpringerLink
Log in

Basic isotopic hydrogen exchange of heteroaromatic compounds (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Research on basic isotopic hydrogen exchange of the methyl groups and aromatic ring CH bonds in various classes of five- and six-membered heterocyclic compounds is examined. Principal attention is directed to the problem of the applicability of correlation and quantumchemical approaches to the establishment of the interrelationship between CH acidity and the peculiarities of the electronic structures of the molecules. The effect of a solvent on the change in the kinetic characteristics of the deuterium exchange of nitrogen-containing heterocycles is discussed.

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. A. I. Shatenshtein, Isotopic Exchange and Substitution of Hydrogen in Organic Compounds [in Russian], Izd. Akad. Nauk SSSR, Moscow (1960).

    Google Scholar 

  2. D. J. Cram, Fundamentals of Carbanion Chemistry, Academic Press (1965).

  3. H. F. Ebel, Die AciditÄt der CH-SÄuren, Georg Thieme Verlag, Stuttgart (1969).

    Google Scholar 

  4. A. I. Shatenshtein, Adv. Phys. Org. Chem., 1, 156 (1963).

    Google Scholar 

  5. A. Streitwieser and D. Hammons, in: New Problems in Physical Organic Chemistry [Russian translation], Mir, Moscow (1967).

    Google Scholar 

  6. A. I. Shatenshtein and I. O. Shapiro, Usp. Khim., 37, 1946 (1968).

    Google Scholar 

  7. M. Bologa, Stud. Cercet. Chim., 19, 1069 (1971).

    Google Scholar 

  8. J. R. Jones, Progr. Org. Chem., 9, 241 (1972).

    Google Scholar 

  9. M. Bologa and E. Gârd, Stud. Cert. Chim., 19, 1329 (1971).

    Google Scholar 

  10. H. Kauffmann, Angew. Chem., Intern. Ed., 4, 543 (1965).

    Google Scholar 

  11. N. N. Zatsepina, Master's Dissertation, Leningrad (1964).

  12. I. F. Tupitsyn, Doctoral Dissertation, Leningrad (1969).

  13. J. A. Zoltewicz and C. L. Smith, J. Amer. Chem. Soc., 88, 4766 (1966).

    Google Scholar 

  14. R. Breslow, J. Amer. Chem. Soc., 79, 1762 (1957).

    Google Scholar 

  15. R. A. Olofson, W. R. Thompson, and J. S. Michelman, J. Amer. Chem. Soc., 86, 1865 (1964).

    Google Scholar 

  16. A. Kharash, J. Org. Chem., 4, 442 (1939).

    Google Scholar 

  17. H. Erlenmeyer, H. M. Wber, and P. Wiessmer, Helv. Chim. Acta, 21, 863, 1017 (1938).

    Google Scholar 

  18. T. I. Abramovich, I. P. Gragerov, and V. V. Perekalin, Dokl. Akad. Nauk SSSR, 121, 295 (1958).

    Google Scholar 

  19. T. I. Abramovich, I. P. Gragerov, and V. V. Perekalin, Zh. Obshch. Khim, 31, 1962 (1961).

    Google Scholar 

  20. A. Streitwieser, W. C. Langworthey, and S. van Sickle, J. Amer. Chem. Soc., 84, 251 (1962).

    Google Scholar 

  21. I. F. Tupitsyn, N. N. Zatsepina, and A. A. Musakin, in: Research in Thermodynamics and Kinetics [in Russian], No. 54, Khimiya, Leningrad (1966), p. 150.

    Google Scholar 

  22. A. I. Shatenshtein and F. S. Yakushin, Kintika i Kataliz, 1, 489 (1960).

    Google Scholar 

  23. N. N. Zatsepina, I. F. Tupitsyn, and L. S. éfros, Zh. Obshch. Khim., 33, 2705 (1963).

    Google Scholar 

  24. N. N. Zatsepina, I. F. Tupitsyn, and L. S. éfros, Zh. Obshch. Khim., 34, 4067, 4073 (1964).

    Google Scholar 

  25. N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 4, 433 (1967).

    Google Scholar 

  26. N. N. Zatsepina, A. A. Kane, and I. F. Tupitsyn, in: Research in Thermodynamics and Kinetics of Chemical Processes [in Russian], GIPKh, Leningrad (1974), p. 59.

    Google Scholar 

  27. A. I. Shatenshtein, E. A. Kovrizhnykh, and I. O. Shapiro, Khim. Geterotsikl. Soedin., 1000 (1971).

  28. A. Streítwíeser and P. J. Scannon, J. Amer. Chem. Soc., 95, 6273 (1973).

    Google Scholar 

  29. W. N. White and D. Lazdins, J. Org. Chem., 34, 2756 (1969).

    Google Scholar 

  30. N. N. Zatsepina, A. V. Kirova, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 5, 70 (1968).

    Google Scholar 

  31. Y. Kawazoe, M. Ohnishi, and Y. Yoshioka, Chem. Pharm. Bull. (Tokyo), 15, 1225 (1967).

    Google Scholar 

  32. Y. Kawazoe, Y. Yoshioka, M. Yamada, and H. Jgeta, Chem. Pharm. Bull. (Tokyo), 15, 2000 (1967).

    Google Scholar 

  33. N. N. Zatsepina and I. F. Tupitsyn, Isotopenpraxis, 3, 103 (1967).

    Google Scholar 

  34. N. N. Zatsepina, I. F. Tupitsyn, Yu. L. Kaminskii, and N. S. Kolodina, Reakts. Sposobnost' Organ. Soedin., 6, 766 (1969).

    Google Scholar 

  35. J. A. White and R. C. Anderson, J. Heterocycle. Chem., 6, 199 (1969).

    Google Scholar 

  36. S. D. Sokolov and V. N. Setkina, Khim. Geterotsikl. Soedin., 786 (1969).

  37. N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 6, 442 (1969).

    Google Scholar 

  38. N. N. Zatsepina, A. V. Korova, N. S. Kolodina, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 7, 667 (1970).

    Google Scholar 

  39. T. J. Batterham, D. J. Brown, and M. N. Paddon-Row, J. Chem. Soc., B, 171 (1967).

  40. E. Gârd, J. Stanoiu, and A. T. Balaban, Rev. Roumaine Chim., 14, 247 (1969).

    Google Scholar 

  41. E. Gârd, A. Vasilescu, G. D. Mateescu, and A. T. Balaban, J. Labelled Compounds, 3, 196 (1967).

    Google Scholar 

  42. A. Streitwieser, Molecular Orbital Theory for Organic Chemists, Wiley (1961).

  43. M. N. Adamov, A. A. Kane, and I. F. Tupitsyn, Teor. i éksperim. Khim., 3, 437 (1967).

    Google Scholar 

  44. P. Berner, H. Köhler, and C. Weiss, Z. Chem., 11, 117 (1971).

    Google Scholar 

  45. A. Streitwieser, P. C. Mowery, R. G. Jesaitis, J. R. Wright, P. H. Owens, and D. M. Renben, Quantum Aspects of Heterocyclic Compounds in Chemistry and Biochemistry (The Jerusalem Symposia on Quantum Chemistry), edited by E. Bergmann and B. Pullman, Vol. 2, Jerusalem (1970), p. 160.

  46. H. H. Jaffe and H. L. James, Adv. Heterocyclic Chemistry, 3, 209 (1964).

    Google Scholar 

  47. I. F. Tupitsyn, N. N. Zatsepina, N. S. Kolodina, and A. A. Kane, Reakts. Sposobnost' Organ. Soedin., 5, 931 (1968).

    Google Scholar 

  48. M. Leveris and J. Miller, J. Chem. Soc., 3486 (1963).

  49. A. R. Katritzky and F. J. Swinbourne, J. Chem. Soc., 6707 (1965).

  50. I. F. Tupitsyn, N. N. Zatsepina, and N. S. Kolodina, Reakts. Sposobnost' Organ. Soedin., 6, 11 (1969).

    Google Scholar 

  51. A. R. Katritzky, C. R. Palmer, F. J. Swinbourne, T. T. Tidwell, and R. D. Topson, J. Amer. Chem. Soc., 91, 636 (1969).

    Google Scholar 

  52. N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 6, 778 (1969).

    Google Scholar 

  53. I. F. Tupitsyn, N. N. Zatsepina, N. S. Kolodina, and Yu. L. Kaminskii, Reakts. Sposobnost' Organ. Soedin., 6, 457 (1969).

    Google Scholar 

  54. D. Dolman and R. Stewart, Can. J. Chem., 45, 911 (1967).

    Google Scholar 

  55. P. Bellingham, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., B, 866 (1968).

  56. G. Marino, Usp. Khim., 42, 577 (1973).

    Google Scholar 

  57. R. Baker, C. Eaborn, and R. Taylor, J. Chem. Soc., Perkin II, 97 (1972).

    Google Scholar 

  58. N. N. Zatsepina, I. F. Tupitsyn, and A. V. Kirova, Reakts. Sposbnost' Organ. Soedin., 9, 195 (1972).

    Google Scholar 

  59. C. Weiss, Z. Chem., 12, 193 (1972).

    Google Scholar 

  60. S. M. Shein and L. A. Kozorez, Reakts. Sposobnost' Organ. Soedin., 9, 195 (1972).

    Google Scholar 

  61. E. Ochiai, Aromatic Amine Oxides, Elsevier Publishing Company, Amsterdam-London-New York (1967).

    Google Scholar 

  62. A. I. Shatenshtein and E. A. Gwosdeva, Tetrahedron, 25, 2749 (1969).

    Google Scholar 

  63. W. G. Salmond, Quart. Rev., 22, 253 (1968).

    Google Scholar 

  64. E. J. Vincent, R. Phan-Tan-Luu, and J. Metzger, Bull. Soc. Chim. France, 3530 (1966).

  65. A. J. H. Wachters, Tetrahedron, 20, 2841 (1964).

    Google Scholar 

  66. D. S. Sappenfield and M. Kreevoy, Tetrahedron, 19, Suppl. 2. 157 (1963).

    Google Scholar 

  67. D. Spinelli, G. Gnanti, and C. Dell'Erba, J. Chem. Soc., Perkin II, 441 (1972).

    Google Scholar 

  68. J. Elguero, E. Gonzalez, J. L. Imbach, and R. Jacquier, Bull. Soc. Chim. France, 4075 (1969).

  69. A. D. Campbell, E. Chan, S. Y. Chooi, L. W. Deady, and R. A. Shanks, J. Chem. Soc., B, 1063, 1069, 1078 (1970).

    Google Scholar 

  70. V. P. Mamaev, O. A. Zagulyaev, and V. P. Krivolapov, Dokl. Akad. Nauk SSSR, 193, 600 (1970).

    Google Scholar 

  71. G. Illuninati, G. Marino, and G. Sleiter, J. Amer. Chem. Soc., 89, 2510 (1967).

    Google Scholar 

  72. N. N. Zatsepina, I. F. Tupitsyn, A. V. Korova, and A. I. Belyashova, Reakts. Sposobnost' Organ. Soedin., 6, 257 (1969).

    Google Scholar 

  73. P. R. Wells, E. Ehrenson, and R. W. Taft, Progr. Phys. Org. Chem., 6, 147 (1968).

    Google Scholar 

  74. M. Charton, J. Org. Chem., 30, 3341, 3346 (1965).

    Google Scholar 

  75. N. N. Zatsepina, I. F. Tupitsyn, V. P. Dushina, Yu. M. Kapustin, and Yu. L. Kaminskii, Reakts. Sposobnost' Organ. Soedin., 9, 745 (1972).

    Google Scholar 

  76. M. J. S. Dewar and P. J. Grisdale, J. Amer. Chem. Soc., 84, 3548 (1962).

    Google Scholar 

  77. N. N. Zatsepina, I. F. Tupitsyn, and N. S. Kolodina, Reakts. Sposobnost' Organ. Soedin., 10, 687 (1973).

    Google Scholar 

  78. D. J. Cram and D. H. Hunter, J. Amer. Chem. Soc., 86, 5478 (1964).

    Google Scholar 

  79. C. E. Hall, R. Piccolini, and J. D. Roberts, J. Amer. Chem. Soc., 77, 4540 (1955).

    Google Scholar 

  80. Yu. I. Ranneva,and A. I. Shatenshtein, in: Correlation Equations in Organic Chemistry [in Russian], Vol. 1, Tartu (1962), p. 136.

    Google Scholar 

  81. A. Streitwieser and R. G. Lawler, J. Amer. Chem. Soc., 85, 2854 (1963).

    Google Scholar 

  82. N. N. Zatsepina and I. F. Tupitsyn, Isotopernpraxis, 3, 269 (1967).

    Google Scholar 

  83. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, and Yu. M. Kapustin, Reakts. Sposobnost' Organ. Soedin., 5, 601 (1968).

    Google Scholar 

  84. I. F. Tupitsyn, N. N. Zatsepina, Yu. M. Kapustin, and A. V. Kirova, Reakts. Sposobnost' Organ. Soedin., 5, 613 (1968).

    Google Scholar 

  85. I. F. Tupitsyn, N. N. Zatsepina, and A. V. Kirova, Reakts. Sposobnost' Organ. Soedin., 5, 626 (1968).

    Google Scholar 

  86. I. F. Tupitsyn, N. N. Zatsepina, A. V. Kirova, Yu. L. Kaminskii, and A. G. Ivanenko, Reakts. Sposobnost' Organ. Soedin., 10, 143 (1973).

    Google Scholar 

  87. J. A. Zoltewicz and C. L. Smith, Tetrahedron, 25, 4331 (1969).

    Google Scholar 

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

    Google Scholar 

  89. J. A. Zoltewicz, C. L. Smith, and G. M. Kauffman, J. Heterocycl. Chem., 8, 337 (1971).

    Google Scholar 

  90. J. A. Zoltewicz and L. S. Helmick, J. Amer. Chem. Soc., 92, 7547 (1970).

    Google Scholar 

  91. J. A. Zoltewicz and G. M. Kauffman, J. Org. Chem., 34, 1405 (1969).

    Google Scholar 

  92. J. A. Zoltewicz and C. L. Smith, Tetrahedron Lett., 337 (1967).

  93. J. A. Zoltewicz and C. L. Smith, J. Amer. Chem. Soc., 89, 3358 (1967).

    Google Scholar 

  94. R. A. Abramovitch, G. M. Singer, and H. R. Vinuthe, Chem. Commun., 55 (1967).

  95. W. W. Paudler and S. A. Humphrey, J. Org. Chem., 35, 3467 (1970).

    Google Scholar 

  96. S. Kruger and W. W. Paudler, J. Org. Chem., 37, 4188 (1972).

    Google Scholar 

  97. R. Guthrie and D. Wesley, J. Amer. Chem. Soc., 92, 4057 (1970).

    Google Scholar 

  98. I. F. Tupitsyn and N. K. Semenova, Research in Thermodynamics and Kinetics of Chemical Processes [in Russian], No. 49, GIPKh (1962), p. 120.

    Google Scholar 

  99. I. F. Tupitsyn, N. N. Zatsepina, N. S. Kolodina, and A. V. Kirova, Reakts. Sposobnost' Organ. Soedin., 9, 1075 (1972).

    Google Scholar 

  100. G. O. Edwards, Usp. Khim., 32, 248 (1963).

    Google Scholar 

  101. J. A. Zoltewicz and L. W. Deady, J. Amer. Chem. Soc., 94, 2754 (1972).

    Google Scholar 

  102. N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 6, 753 (1969).

    Google Scholar 

  103. A. I. Shatenshtein, I. O. Shapiro, Yu. I. Ranneva, and A. G. Kamrad, Reakts. Sposobnost' Organ. Soedin., 1, 232 (1964).

    Google Scholar 

  104. A. I. Shatenshtein, A. G. Kamrad, I. O. Shapiro, Yu. I. Ranneva, and E. N. Zvyagintseva, Dokl. Akad. Nauk SSSR, 168, 364 (1966).

    Google Scholar 

  105. A. G. Kamrad and A. I. Shatenshtein, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 587 (1963).

  106. A. I. Shatenshtein and E. A. Gvozdeva, Teor. i éksperim. Khim., 1, 352 (1965).

    Google Scholar 

  107. R. A. Olofson, J. M. Landesberg, K. N. Houk, and J. S. Michelman, J. Amer. Chem. Soc., 88, 4265 (1966).

    Google Scholar 

  108. R. A. Coburn, J. M. Landesberg, D. S. Kemp, and R. A. Olofson, Tetrahedron, 26, 685 (1970).

    Google Scholar 

  109. R. H. Erlich and A. I. Popov, J. Phys. Chem., 74, 338 (1970).

    Google Scholar 

  110. T. J. Curphey, J. Amer. Chem. Soc., 87, 2064 (1965).

    Google Scholar 

  111. T. Harris and J. Rendell, Chem. Ind., 1728 (1965).

  112. W. P. Norris and R. A. Henry, Tetrahedron Lett., 1213 (1965).

  113. J. Vaughan, Z. Munghrabi, and E. C. Wu, J, Org. Chem., 35, 1141 (1970).

    Google Scholar 

  114. J. Brown and P. B. Chosh, J. Chem. Soc., B, 270 (1969).

  115. H. A. Staab, M. Wu, A. Mannschreck, and G. Schalbach, Tetrahedron Lett., 845 (1964).

  116. J. A. Elvidge, J. R. Jones, C. O'Brien, E. A. Evans, and J. C. Turner, J. Chem. Soc., Perkin II, 432 (1973).

  117. M. Foa, F. Toddei, and P. E. Todesco, Boll. Sci. Fac. Chim. Ind. Bologna, 23, 225, 229 (1965).

    Google Scholar 

  118. R. A. Olofson and J. M. Landesberg, J. Amer. Chem. Soc., 88, 4263 (1966).

    Google Scholar 

  119. A. C. Rochat and R. A. Olofson, Tetrahedron Lett., 3377 (1969).

  120. H. Kohn, S. J. Benkovic, and R. A. Olofson, J. Amer. Chem. Soc., 94, 5759 (1972).

    Google Scholar 

  121. P. Haake, L. P. Bausher, and M. B. Miller, J. Amer. Chem. Soc., 91, 113 (1969).

    Google Scholar 

  122. D. S. Kemp and J. T. O'Brien, J. Amer. Chem. Soc., 92, 2554 (1970).

    Google Scholar 

  123. J. Crosby and G. Lienhard, J. Amer. Chem. Soc., 92, 5707 (1970).

    Google Scholar 

  124. N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobnost' Organ. Soedin., 6, 448 (1969).

    Google Scholar 

  125. A. I. Shatenshtein, N. N. Magdesieva, Yu. I. Ranneva, I. O. Shapiro, and A. I. Serebryanskaya, Teor.i. éksperim. Khim., 3, 343 (1967).

    Google Scholar 

  126. A. I. Shatenshtein, Ya. L. Gol'dfarb, I. O. Shapiro, E. N. Zvyagintseva, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR, 180, 1379 (1968).

    Google Scholar 

  127. A. I. Shatenshtein, A. G. Kamrad, I. O. Shapiro, and Yu. I. Ranneva, Khim. Geterotsilk. Soedin., 643 (1966).

  128. T. A. Yakushina, I. O. Shapiro, E. N. Zvyagintseva, V. P. Litvinov, S. A. Ozolin', Ya. L. Gol'dfarb, and A. I. Shatenshtein, Zh. Obshch. Khim., 41, 1930 (1971).

    Google Scholar 

  129. W. W. Paudler and L. S. Helmick, Chem. Commun., 377 (1967).

  130. W. W. Paudler and L. S. Helmick, J. Org. Chem., 33, 1087 (1968).

    Google Scholar 

  131. E. N. Zvyagintseva, T. A. Yakushina, and A. I. Shatenshtein, Zh. Obshch. Khim., 38, 1998 (1968).

    Google Scholar 

  132. E. N. Zvyagintseva, L. I. Belen'kii, T. A. Yakushina, Ya. L. Gol'dfarb, and A. I. Shatenshtein, Zh. Obshch. Khim., 38, 2004 (1968).

    Google Scholar 

  133. E. N. Zvyagintseva, D. S. Gorbenko-Germanov, and A. I. Shatenshtein, Zh. Obshch. Khim., 40, 1152 (1970).

    Google Scholar 

  134. T. A. Yakushina, E. N. Zvyagintseva, V. P. Litvinov, S. A. Ozolin', Ya. L. Gol'dfarb, and A. I. Shatenshtein, Zh. Obshch. Khim., 40, 1622 (1970).

    Google Scholar 

  135. D. J. Cram, B. Rickborn, C. A. Kingsbury, and P. Haferfield, J. Amer. Chem. Soc., 83, 3648 (1961).

    Google Scholar 

  136. A. I. Shatenshtein and I. O. Shapiro, Teor. i éksperim. Khim., 5, 59 (1969).

    Google Scholar 

  137. Yu. I. Ranneva and A. I. Shatenshtein, Zh. Obshch. Khim., 42, 1812, 2250 (1972).

    Google Scholar 

  138. J. F. Goetree and C. D. Ritchie (editors), Solute-Solvent Interactions, Wiley, New York (1969).

    Google Scholar 

  139. C. D. Ritchie and R. E. Uschold, J. Amer. Chem. Soc., 89, 2960 (1967).

    Google Scholar 

  140. A. I. Shatenshtein and E. N. Zvyagintseva, Dokl. Akad. Nauk SSSR, 117, 852 (1958).

    Google Scholar 

  141. I. F. Tupitsyn, N. N. Zatsepina, A. V. Korova, and Yu. M. Kapustin, Reakts. Sposobnost' Organ. Soedin., 5, 806 (1968).

    Google Scholar 

  142. O. A. Reutov, I. P. Beletskaya, and K. P. Butin, Usp. Khim., 18, 35 (1974).

    Google Scholar 

  143. I. F. Tupitsyn, N. N. Zatsepina, A. V. Korova, and Yu. M. Kapustin, Reakts. Sposobnost' Organ. Soedin., 5, 836 (1968).

    Google Scholar 

  144. L. G. Hepler, J. Amer. Chem. Soc., 85, 3089 (1963).

    Google Scholar 

  145. B. C. Challis and E. M. Miller, J. Chem. Soc., Perkin II, 1111 (1972).

    Google Scholar 

  146. Y. Kawazoe, M. Ohnishi, and Y. Yasioka, Chem. Pharm. Bull. (Tokyo), 12, 1384 (1964).

    Google Scholar 

  147. V. P. Lezina, A. U. Stepanyants, L. D. Smirnov, and K. M. Dyumaev, Izv: Akad. Nauk SSSR, Ser. Khim., 1208 (1972).

  148. V. P. Lezina, A. U. Stepanyants, L. D. Smirnov, N. A. Andronova, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1224 (1972).

Download references

Author information

Authors and Affiliations

  1. State Institute of Applied Chemistry, Leningrad

    N. N. Zatsepina & I. F. Tupitsyn

Authors
  1. N. N. Zatsepina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. F. Tupitsyn
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1587–1612, December, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zatsepina, N.N., Tupitsyn, I.F. Basic isotopic hydrogen exchange of heteroaromatic compounds (review). Chem Heterocycl Compd 10, 1397–1417 (1974). https://doi.org/10.1007/BF00474317

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00474317

Keywords

Search

Navigation