Chemistry of Heterocyclic Compounds

, Volume 13, Issue 9, pp 963–968 | Cite as

Isotopic hydrogen exchange in methyl derivatives of five-membered aromatic heterocycles

  • N. N. Zatsepina
  • I. F. Tupitsyn
  • A. I. Belyashova
  • A. V. Kirova
  • E. Ya. Konyakhina
Article
  • 27 Downloads

Abstract

The kinetics of isotopic exchange of the hydrogen atoms of the methyl groups in an alcohol solution of potassium ethoxide were studied for an extensive series of methyl derivatives of azoles and di-, tri-, and tetrazoles. The electronic effect of one or several heteroatoms and substituents on the rate of deuterium exchange of five-membered heterocycles is satisfactorily conveyed by the correlation relationship previously established for a series of substituted toluenes and six-membered heteroaromatic compounds (ρ25°=7.6). The limitations that exist in a number of cases are discussed in connection with the peculiarities of the electron-density distribution in five- and six-membered heterocycles.

Keywords

Hydrogen Atom Deuterium Tetrazoles Azole Ethoxide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    N. N. Zatsepina, I. F. Tupitsyn, A. I. Belyashova, A. A. Kane, N. S. Kolodina, and G. N. Sudakova, Khim. Geterotsikl. Soedin., No. 8, 1110 (1977).Google Scholar
  2. 2.
    N. N. Zatsepina, I. F. Tupitsyn, A. A. Kane, and G. N. Sudakova, Khim. Geterotsikl. Soedin., No. 9, 1192 (1977).Google Scholar
  3. 3.
    J. A. White and R. C. Anderson, J. Heterocycl. Chem., 6, 199 (1969).Google Scholar
  4. 4.
    S. D. Sokolov and V. N. Setkina, Khim. Geterotsikl. Soedin., No. 5, 786 (1969).Google Scholar
  5. 5.
    N. N. Zatsepina, I. F. Tupitsyn, Yu. L. Kaminskii, and N. S. Kolodina, Reakts. Sposobn. Org. Soedin., 6, 766 (1969).Google Scholar
  6. 6.
    N. N. Zatsepina and I. F. Tupitsyn, Khim. Geterotsikl. Soedin., No. 12, 1587 (1974).Google Scholar
  7. 7.
    N. N. Zatsepina, I. F. Tupitsyn, and A. V. Kirova, Reakts. Sposobn. Org. Soedin., 9, 195 (1972).Google Scholar
  8. 8.
    N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobn. Org. Soedin., 4, 433 (1967).Google Scholar
  9. 9.
    N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobn. Org. Soedin., 6, 753 (1969).Google Scholar
  10. 10.
    N. N. Zatsepina, Yu. L. Kaminskii, and I. F. Tupitsyn, Reakts. Sposobn. Org. Soedin., 6, 778 (1969).Google Scholar
  11. 11.
    D. Spinelli, G. Gnanti, and C. Dell'Erba, J. Chem. Soc., Perkin II, No. 4, 441 (1972).Google Scholar
  12. 12.
    G. B. Berlin, J. Chem. Soc. (B), No. 7, 641 (1967).Google Scholar
  13. 13.
    R. P. Kirkjy and E. V. Brown, J. Am. Chem. Soc., 74, 5778 (1952).Google Scholar
  14. 14.
    L. Claisen, Ber., 24, 3900 (1895).Google Scholar
  15. 15.
    N. K. Kochetkov, S. D. Sokolov, and N. M. Vagurtova, Zh. Obshch. Khim., 31, 2330 (1961).Google Scholar
  16. 16.
    H. J. Jarg, J. Indian Chem. Soc., 40, 135 (1963).Google Scholar
  17. 17.
    P. C. Jocelyn, J. Chem. Soc., No. 7, 3305 (1957).Google Scholar
  18. 18.
    V. K. Bhagwat and F. L. Pyman, J. Chem. Soc., 1832 1925.Google Scholar
  19. 19.
    Societe des Usines Chimiques Phone-Roulen, British Patent No. 837838 (1960); Chem. Abstr., 54, P24804iGoogle Scholar
  20. 20.
    N. I. Kudryashova, N. V. Khromov-Borisov, M. N. Bobrova, and T. A. Mikhailova, Zh. Obshch. Khim., 33, 173 (1963).Google Scholar
  21. 21.
    I. I. Grandberg, S. N. Milovanova, A. N. Kost, and I. T. Nette, Vestn. Mosk. Gos. Univ., Ser. 6, 16, 27 (1961).Google Scholar
  22. 22.
    J. T. Morgan and G. Ackerman, J. Chem. Soc., 123, 1312 (1923).Google Scholar
  23. 23.
    L. Behr and G. Brent, Organic Syntheses, Vol. 34 (ed. by N. Rabjohn), Wiley-Interscience (1963).Google Scholar
  24. 24.
    Ya. A. Levin and M. S. Skorobogatova, Khim. Geterotsikl. Soedin., No. 6, 1128 (1967).Google Scholar
  25. 25.
    M. Ohta and H. Kimoto, J. Pharm. Soc. Jpn., 16, 10 (1956).Google Scholar
  26. 26.
    M. R. Atkinson and J. B. Polva, J. Chem. Soc., No. 1, 141 (1954).Google Scholar
  27. 27.
    N. N. Zatsepina, I. F. Tupitsyn, and L. S. Éfros, in: Chemistry and Technology of Isotopes [in Russian], No. 56, Khimiya (1967), p. 113.Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • N. N. Zatsepina
    • 1
  • I. F. Tupitsyn
    • 1
  • A. I. Belyashova
    • 1
  • A. V. Kirova
    • 1
  • E. Ya. Konyakhina
    • 1
  1. 1.State Institute of Applied ChemistryLeningrad

Personalised recommendations