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


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.


Spectroscopy Ester Ethyl Hydroxyl Organic Chemistry 
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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

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