Chemistry of Heterocyclic Compounds

, Volume 9, Issue 7, pp 799–801 | Cite as

The law of the reactions of trans-2-ethoxy-3,4-epoxyteteahydropyran with some nucleophiles containing a mobile hydrogen atom

  • V. B. Mochalin
  • A. N. Kornilov
  • B. V. Unkovskii


In order to investigate the laws of the opening of the α-oxide ring of epoxides of the tetrahydropyran series with nucleophilic reagents, we have studied the reactions of trans-2-ethoxy-3,4-epoxytetrahydropyran with some nucleophiles containing a mobile hydrogen atom — hydrogen cyanide, hydrogen sulfide, and benzimidazole. The reactions investigated have a strictly directed nature and lead to the formation of 3-substituted ethyl-3,4-di-deoxy-α-DL-threo-pentapyranosides, exclusively.


Hydrogen Sulfide Organic Chemistry Hydrogen Atom Cyanide 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. B. Mochalin, Z. I. Smolina, and B. V. Unkovskii, Zh. Organ. Khim., 5, 2224 (1969).Google Scholar
  2. 2.
    M. Cahu and G. Descotes, Bull. Soc. Chim. France, 2975 (1968).Google Scholar
  3. 3.
    F. Sweet and R. K. Brown, Can. J. Chem., 46, 1592 (1968).Google Scholar
  4. 4.
    B. I. Ionin and B. A. Ershov, NMR Spectroscopy in Organic Chemistry [in Russian], Khimiya, Leningrad (1967), pp. 222, 228.Google Scholar
  5. 5.
    H. Spedding, J. Chem. Soc., 3617 (1961).Google Scholar
  6. 6.
    S. A. Barker, J. S. Brimacombe, A. B. Foster, D. H. Whiffen, and G. Zweifel, Tetrah., 7, 10 (1959).Google Scholar
  7. 7.
    A. Fürst and P. A. Plattner, Abstracts of Papers, 12th International Congress of Pure and Applied Chemistry, New York (1951), p. 409.Google Scholar
  8. 8.
    F. Sweet and R. K. Brown, Can. J. Chem., 46, 1481 (1968).Google Scholar
  9. 9.
    V. B. Mochalin, Yu. N. Porshnev, and G. I. Samokhvalov, Zh. Obshch. Khim., 38, 85 (1968).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • V. B. Mochalin
    • 1
  • A. N. Kornilov
    • 1
  • B. V. Unkovskii
    • 1
  1. 1.M. V. Lomonosov Moscow Institute of Fine Chemical TechnologyUSSR

Personalised recommendations