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Reactions involving isotopic exchange of heterocyclic compounds with D2O in the presence of transition metals (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The results of isotopic exchange with D2O of various O-, N-, and S-containing heterocycles and some hydrocarbons on transition metals are discussed from the positions of the theory of π-complex adsorption. The effect of various fragments of the molecules (the aromatic or alicyclic ring, electron-donor or electron-acceptor substituents, double bonds, and the number and nature of the heteroatoms) on the character of the substrate-catalyst interaction and on the reaction as a whole is examined on the basis of kinetic data from 1H and 13C NMR spectroscopy and Chromatographic mass spectrometry. Isotopic exchange mechanisms are discussed.

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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. M. Bologa and E. Gard, Stud. Cercet. Chim., 19, 1329 (1971).

    Google Scholar 

  3. H. Kauffman, Angew. Chem., Ed., 4, 543 (1965).

    Google Scholar 

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

    Google Scholar 

  5. R. Breslow, J. Am. Chem. Soc., 79, 1769 (1957).

    Google Scholar 

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

    Google Scholar 

  7. J. L. Garnett and W. A. Sollich-Baumgartner, in: Catalysis [Russian translation], Mir, Moscow (1968), p. 100.

    Google Scholar 

  8. G. K. Bond and M. B. Wells, in: Catalysis [Russian translation], Mir, Moscow (1967), p. 351.

    Google Scholar 

  9. G. D. Zakumbaeva, Interaction of Organic Compounds with the Surface of Group VIII Metals [in Russian], Nauka, Alma-Ata (1978).

    Google Scholar 

  10. V. Ponec and W. H. H. Sachler, J. Catal., 24, 250 (1972).

    Google Scholar 

  11. J. L. Vlasveld and V. Ponec, J. Catal., 44, 352 (1976).

    Google Scholar 

  12. R. Montarnal and G. Martino, Rev. Inst. Fr. Petrole, 32, No. 3, 367 (1977).

    Google Scholar 

  13. C. Kemball, in: Catalysis [Russian translation], Inostr. Lit., Moscow (1963), p. 247.

    Google Scholar 

  14. A. V. Sklyarov, Problems in Kinetics and Catalysis [in Russian], Nauka, Moscow (1975), No. 16, p. 238.

    Google Scholar 

  15. R. B. Moyes and P. B. Wells, Adv. Catal., 23, 121 (1973).

    Google Scholar 

  16. J. L. Garnett, Catal. Rev., 5 (2), 229 (1971).

    Google Scholar 

  17. R. Kh. Burshtein, A. G. Pshenichnikov, V. S. Tyurin, and A. A. Michri, in: Catalytic Reactions in the Liquid Phase [in Russian], Nauka, Alma-Ata (1967).

    Google Scholar 

  18. R. P. Eischens and W. A. Pliskin, Adv. Catalysis, 10, 1 (1958).

    Google Scholar 

  19. P. W. Selwood, Adsorption and Collective Paramagnetism, Academic Press, New York (1962).

    Google Scholar 

  20. G. N. Denisov, V. A. Kolyagin, V. D. Yagodovskii, and V. M. Gryaznov, Kinet. Katal., 18, 704 (1977).

    Google Scholar 

  21. M. V. Gomoyunova, Zh. Tekhn. Fiz., 47, 673 (1977).

    Google Scholar 

  22. G. K. Konn and G. H. Twigg, Proc. Roy. Soc., A-171, 70 (1939).

    Google Scholar 

  23. L. H. Little, N. Sheppard, and D. Y. Yates, Proc. Roy. Soc., A-259, 242 (1960).

    Google Scholar 

  24. B. A. Morrow and N. Sheppard, J. Phys. Chem., 70, 2406 (1966).

    Google Scholar 

  25. V. N. Korchak, I. I. Tret'yakov, and M. U. Kislyuk, Kinet. Katal., 17, 983 (1976).

    Google Scholar 

  26. J. J. Rooney and G. Webb, J. Catal., 3, 488 (1964).

    Google Scholar 

  27. G. C. Bond, Catalysis by Metals, Academic Press, New York (1962).

    Google Scholar 

  28. G. C. Bond, Discuss. Faraday Soc., 41, 200 (1966).

    Google Scholar 

  29. R. Merta and V. Ponec, in: Fundamentals of the Prediction of Catalytic Action (Proceedings of the 4th International Congress on Catalysis) [in Russian], Vol. 4, Nauka, Moscow (1970), p. 84.

    Google Scholar 

  30. A. E. Morgan and G. C. Somorjiai, J. Chem. Phys., 51, 3309 (1969).

    Google Scholar 

  31. D. L. Smith and R. P. Merrill, J. Chem. Phys., 52, 5861 (1970).

    Google Scholar 

  32. E. Krawford and C. Kemball, Trans. Faraday Soc., 58, 2452 (1962).

    Google Scholar 

  33. J. L. Garnett and W. A. Sollich, J. Catal., 2, 350 (1963).

    Google Scholar 

  34. J. L. Garnett and W. A. Sollich-Baumgartner, J. Phys. Chem., 68, 3177 (1964).

    Google Scholar 

  35. K. Kishi and S. Ikeda, J. Phys. Chem., 73, 2559 (1969).

    Google Scholar 

  36. R. B. Moyes and P. B. Wells, J. Catal., 21, 86 (1971).

    Google Scholar 

  37. R. A. Ashby and J. L. Garnett, Aust. J. Chem., 16, 549 (1963).

    Google Scholar 

  38. G. E. Calf, J. L. Garnett, and V. A. Pickles, Aust. J. Chem., 21, 961 (1968).

    Google Scholar 

  39. G. E. Calf and J. L. Garnett, Aust. J. Chem., 21, 1221 (1968).

    Google Scholar 

  40. G. E. Calf and J. L. Garnett, Chem. Commun., 306 (1967).

  41. J. L. Garnett, W. A. Sollich, and G. V. D. Tiers, Tetrahedron Lett., No. 15, 516 (1961).

    Google Scholar 

  42. J. L. Garnett and W. A. Sollich, Aust. J. Chem., 15, 56 (1964).

    Google Scholar 

  43. J. L. Garnett, L. J. Henderson, and W. A. Sollich, Tritium in the Physical and Biological Sciences, Vol. 2, IAEA, Vienna (1962).

    Google Scholar 

  44. J. L. Garnett and W. A. Sollich, Aust. J. Chem., 15, 62 (1962).

    Google Scholar 

  45. G. E. Calf, J. L. Garnett, and W. A. Sollich, Advances in Tracer Methodology, Vol. 4, Plenum Press (1968), p. 11.

  46. É. A. Karakhanov, A. G. Dedov, A. L. Kurts, and A. S. Loktev, Khim. Geterotsikl. Soedin., No. 4, 451 (1981).

    Google Scholar 

  47. J. T. Ernst, J. L. Garnett, and W. A. Sollich, J. Catal., 3, 568 (1964).

    Google Scholar 

  48. J. L. Garnett, in: Proceedings of the Second International Conference on Methods of Preparing and Storing of Labeling Compounds, Brussels (1966), p. 709.

  49. É. A. Karakhanov, A. G. Dedov, and E. A. Viktorova, Vestn. Mosk. Gos. Univ., Khimiya, No. 2, 215 (1977).

    Google Scholar 

  50. C. G. Macdonald and J. S. Schannon, Tetrahedron Lett., No. 21, 1349 (1963).

    Google Scholar 

  51. G. E. Calf and J. L. Garnett, J. Catal., 3, 416 (1964).

    Google Scholar 

  52. L. K. Klaisinic, E. Pop, and N. Trinaistic, Tetrahedron, 28, 3465 (1972).

    Google Scholar 

  53. É. A. Karakhanov, A. G. Dedov, and P. A. Sharbatyan, in: Proceedings of the 4th Soviet- French Seminar on Catalysis [in Russian], Tbilisi (1978), p. 168.

  54. É. A. Karakhanov, A. G. Dedov, Yu. N. Luzikov, E. A. Viktorova, and E. V. Lunina, Dokl. Akad. Nauk SSSR, 243, 1190 (1978).

    Google Scholar 

  55. É. A. Karakhanov, A. G. Dedov, A. L. Kurts, and Yu. N. Luzikov, Dokl. Akad. Nauk SSSR, 256, 1397 (1981).

    Google Scholar 

  56. A. G. Dedov, Master's Dissertation, Moscow State University (1978).

  57. É. A. Karakhanov, A. G. Dedov, L. V. Popov, and E. A. Viktorova, Vestn. Mosk. Gos. Univ., Khimiya, No. 5, 595 (1976).

    Google Scholar 

  58. É. A. Karakhanov, A. G. Dedov, I. I. Pakhomova, A. G. Saginova, and E. A. Viktorova, Vestn. Mosk. Gos. Univ., Khimiya, No. 3, 334 (1977).

    Google Scholar 

  59. É. A. Karakhanov, A. G. Dedov, and A. S. Loktev, Khim. Geterotsikl. Soedin., No. 10, 1332 (1981).

    Google Scholar 

  60. É. A. Karakhanov, A. G. Dedov, and E. V. Lunina, Dokl. Akad. Nauk SSSR, 254, 400 (1980).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1011–1021, August, 1982.

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Karakhanov, É.A., Dedov, A.G. Reactions involving isotopic exchange of heterocyclic compounds with D2O in the presence of transition metals (review). Chem Heterocycl Compd 18, 763–772 (1982). https://doi.org/10.1007/BF00506573

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  • DOI: https://doi.org/10.1007/BF00506573

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