Chemistry of Heterocyclic Compounds

, Volume 14, Issue 7, pp 721–724 | Cite as

Synthesis and stereochemistry of 3-hydroxy-6-perfluoroalkyl-2, 3-dihydro-4-pyrones

  • V. I. Tyvorskii
  • L. S. Stanishevskii
  • I. G. Tishchenko
Article

Abstract

The reaction of a number of aliphatic and alicyclic acetloxiranes with perfluoroalkanoic acid esters was studied. It is shown that substituted 3-hydroxy-6-perfluoroalkyl-2,3-dihydro-4-pyrones are formed. The reverse reaction scheme, including the formation of an intermediate β-diketone and cyclization of its enol form to a dihydropyrone, was confirmed in the case of the condensation of 3-methyl-2,3-epoxycyclohexanone with ethyl trifluoroacetate. The stereochemistry of the reaction products, which exist in a half-chair confirmation with a pseudoequatorial hydroxyl group, was examined by means of PMR spectroscopy.

Keywords

Spectroscopy Ester Ethyl Hydroxyl Organic Chemistry 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. I. Tyvorskii, L. S. Stanishevskii, and I. G. Tishchenko, Khim. Geterotsikl. Soedin., No. 11, 1575 (1976).Google Scholar
  2. 2.
    K. Nakanisi, Infrared Spectra and the Structure of Organic Compounds [Russian translation], Mir, Moscow (1965), p. 52.Google Scholar
  3. 3.
    J. D. Park, H. A. Brown, and J. R. Lacher, J. Am. Chem. Soc., 75, 4753 (1953).Google Scholar
  4. 4.
    G. P. Brandlin and E. T. McBee, Advances in the Chemistry of Fluorine [Russian translation], Vols. 3–4, Khimiya, Leningrad (1970), pp. 242, 243.Google Scholar
  5. 5.
    J. Niwa, M. Yamazaki, and T. Takeuchi, Chem. Lett., No. 7, 707 (1975).Google Scholar
  6. 6.
    J. R. Dyer, Applications of Absorption Spectroscopy of Organic Compounds [Russian translation], Khimiya, Moscow (1970), p. 101.Google Scholar
  7. 7.
    F. Fischer and W. Arlt, Chem. Ber., 97, 1910 (1964).Google Scholar
  8. 8.
    R. C. Anderson and D. M. Gunn, J. Chem. Soc., Chem. Commun., No. 1, 27 (1977).Google Scholar
  9. 9.
    T. G. Fourie, D. Ferreira, and D. G. Roux, J. Chem. Soc., Perkin I, No. 2, 125 (1977).Google Scholar
  10. 10.
    H. Wagner, O. Seligmann, M. Seitz, D. Abraham, and J. Sonnenbichler, Z. Naturforsch., 31B, 876 (1976).Google Scholar
  11. 11.
    F. D. Monache, G. D. Monache, and G. B. Marini-Bettolo, Gazz. Chim. Ital., 106, 935 (1976).Google Scholar
  12. 12.
    L. B. Barkley and R. Levine, J. Am. Chem. Soc., 73, 4625 (1951).Google Scholar
  13. 13.
    Houben-Weyl, Methoden der Organischen Chemie, Vol. 2, Georg Thieme Verlag, Stuttgart (1952–1958).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • V. I. Tyvorskii
    • 1
  • L. S. Stanishevskii
    • 1
  • I. G. Tishchenko
    • 1
  1. 1.V. I. Lenin Belorussian State UniversityMinsk

Personalised recommendations