Advertisement

Chemistry of Heterocyclic Compounds

, Volume 4, Issue 6, pp 748–752 | Cite as

Investigations in heterocyclic chemistry

XLIV. Comparative ease of ring-closure of five- and six-membered heterocycles in the acid condensation of arylides of diarylglycolic acids
  • P. A. Petyunin
  • A. K. Sukhomlinov
  • N. G. Panferova
Article
  • 45 Downloads

Abstract

With the acid condensation of diarylglycolic benzylanilides as an example, it has been shown that the predominant formation of a fivemembered ring rather than a six-membered ring takes place even in the case where the internal structure of the anilide permits the simultaneous formation of both rings. It has also been shown that it is possible to determine the size of the ring formed on condensation from the UV and IR spectra, and the presence of hydrogen bonds in the arylamides of diarylglycolic acids and the formation of the lactim form and of the quatenary ammonium salt of the base of 3, 3-diphenyloxindole in solutions of sodium ethoxide and concentrated H2SO4, respectively, have been confirmed.

Keywords

Hydrogen Sodium Ammonium Hydrogen Bond Organic Chemistry 
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.

References

  1. 1.
    P. A. Petyunin and N. G. Panferova, ZhOKh, 17, 502, 1947.Google Scholar
  2. 2.
    P. A. Petyunin, ZhOKh, 22, 700, 1952.Google Scholar
  3. 3.
    P. A. Petyunin and V. S. Shklyaev, ZhOKh, 23, 853, 1953.Google Scholar
  4. 4.
    W. S. Johnson, Organic Reactions, Vol. 2, [Russian translation], IL, 129, 1950.Google Scholar
  5. 5.
    P. A. Petyunin and N. G. Panferova, KhGS [Chemistry of Heterocyclic Compounds], 2, 734, 1966.Google Scholar
  6. 6.
    P. A. Petyunin and A. F. Soldatova, KhGS [Chemistry of Heterocyclic Compounds], 1, 261, 1965.Google Scholar
  7. 7.
    V. S. Shklyaev, ZhOKh, 35, 1966, 1965.Google Scholar
  8. 8.
    A. Cross, An Introduction to Practical Infrared Spectroscopy [Russian translation], IL, 96, 1961.Google Scholar
  9. 9.
    K. Nakanishi, Absorption Spectroscopy. Practical [Russian translation], Mir, pp. 37, 58, 1965.Google Scholar
  10. 10.
    L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL, p. 293, 1963.Google Scholar
  11. 11.
    T. I. Temnikova, Course of the Theoretical Principles of Organic Chemistry [in Russian], Goskhimizdat, p. 168, 1959.Google Scholar
  12. 12.
    G. Pimentel and O. MacClellan, The Hydrogen Bond [Russian translation], Mir, p. 160, 1964.Google Scholar
  13. 13.
    A. E. Lutskii, Usp. khim., 23, 479, 1954.Google Scholar
  14. 14.
    S. L. Shapiro, I. M. Rose, and L. Freedmann, J. Am. Chem. Soc., 23, 6822, 1959.Google Scholar
  15. 15.
    A. A. Boldin and R. F. Vasil'ev, Zav. lab., 7, 12, 1961.Google Scholar
  16. 16.
    B. Witkop, and A. Ek, J. Am. Chem. Soc., 73, 5664, 1951.Google Scholar
  17. 17.
    M. E. Konshin and P. A. Petyunin, KhGS collection 1, 310, 1967.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • P. A. Petyunin
    • 1
    • 2
  • A. K. Sukhomlinov
    • 1
    • 2
  • N. G. Panferova
    • 1
    • 2
  1. 1.Khar'kov Pharmaceutical InstituteUSSR
  2. 2.Perm Pharmaceutical InstituteUSSR

Personalised recommendations