Advertisement

Chemistry of Natural Compounds

, Volume 7, Issue 4, pp 425–428 | Cite as

Conformational transformations of lupinine in the formation of protonated forms and quaternary salts

  • T. K. Yunusov
  • T. K. Kasymov
  • F. G. Kamaev
  • V. B. Leont'ev
  • K. Inoyatova
  • A. I. Ishbaev
  • A. S. Sadykov
Article
  • 17 Downloads

Summary

  1. 1.

    The results of a study of IR and PMR spectra have shown that in solution protonated lupinine exists in two interconverting cis-trans conformations the relative amounts of which depend on the temperature, the concentrations of base and water, and the pH of the medium. This process is possible because of a change in the direction of the unshared pair of the nitrogen atom in the inversion process.

     
  2. 1.

    On the basis of the PMR and IR spectra, lupinine methiodide has the a,e conformation with an e-CH2OH group and epilupinine methiodide has the a,a conformation with an e-CH2OH group.

     

Keywords

Protonated Form Inversion Process Decalin Methiodide Quinolizidine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    H. I. Aaron, Chem. Ind. (London),30, 1338 (1965).Google Scholar
  2. 2.
    E. Eliel, N. Allinger, S. Angyal, and G. Morrison, Conformational Analysis, Interscience (1965).Google Scholar
  3. 3.
    F. Galinovsky and V. Nesvadba, Monatsh.,85, 1300 (1954).CrossRefGoogle Scholar
  4. 4.
    A. Thomas, H. Vipond, and L. Marion, Canad. J. Chem.,33, 1290 (1955).CrossRefGoogle Scholar
  5. 5.
    T. K. Yunusov, A. I. Ishbaev, V. B. Leont'ev, and A. S. Sadykov, Khim. Prirodn. Soedin.,7, 49 (1971).Google Scholar
  6. 6.
    T. Moynehean, K. Schofield, A. V. Jones, and A. R. Katritzky, J. Chem. Soc., 2637 (1962).Google Scholar
  7. 7.
    W. Grow, Austral. J. Chem.,11, 366 (1958).CrossRefGoogle Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • T. K. Yunusov
  • T. K. Kasymov
  • F. G. Kamaev
  • V. B. Leont'ev
  • K. Inoyatova
  • A. I. Ishbaev
  • A. S. Sadykov

There are no affiliations available

Personalised recommendations