Chemistry of Heterocyclic Compounds

, Volume 20, Issue 2, pp 128–132 | Cite as

Three-dimensional structures of cyclic 2,2-bis(hydroxymethyl)-tetrahydrofuran acetals

  • R. A. Karakhanov
  • M. R. Skurko
  • T. Yu. Solov'eva
  • L. Yu. Brezhnev
  • L. F. Lapuka
  • M. M. Vartanyan
Article
  • 29 Downloads

Abstract

2-Substituted spiro[1,3-dioxane-5,2′-tetrahydrofurans] were obtained from 2,2-bis (hydroxymethyl) tetrahydrofuran, and their three-dimensional structures were investigated by 1H and 13C NMR spectroscopy. The tetrahydrofuran ring lies in the plane of symmetry of the 1,3-dioxane ring with an equatorial orientation of the oxygen atom.

Keywords

Oxygen Spectroscopy Acetal Organic Chemistry Oxygen Atom 

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Literature cited

  1. 1.
    S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, Dokl. Akad. Nauk SSSR, 176, 332 (1967).Google Scholar
  2. 2.
    U. Herrog and B. Reinshagen, Eur. J. Med. Chem., 11, 415 (1976).Google Scholar
  3. 3.
    K. C. Ramey and J. Messiek, Tetrahedron Lett., No. 49, 4423 (1965).Google Scholar
  4. 4.
    M. Anteunis and J. Swaelens, Org. Magn. Reson., 2, 389 (1970).Google Scholar
  5. 5.
    Yu. Yu. Samitov, Z. I. Zelikman, and V. G. Kul'nevich, Zh. Strukt. Khim., 10, 234 (1969).Google Scholar
  6. 6.
    A. S. Yavorskii, Yu. Yu. Samitov, A. V. Bogat-skii, A. I. Gren', and O. S. Stepanova, Zh. Org. Khim., 13, 1103 (1977).Google Scholar
  7. 7.
    M. Anteunis, D. Tabernier, and F. Borremans, Heterocycles, 4, 293 (1976).Google Scholar
  8. 8.
    Yu. Yu. Samitov, Khim. Geterotsikl. Soedin., No. 12, 1587 (1978).Google Scholar
  9. 9.
    K. Pihlaja and P. Ayras, Acta Chem. Scand., 24, 531 (1970).Google Scholar
  10. 10.
    J. Delman and J. Duplan, Tetrahedron Lett., No. 6, 559 (1966).Google Scholar
  11. 11.
    J. Kotowyzg and R. Lemieux, Chem. Rev., 73, 666 (1973).Google Scholar
  12. 12.
    Yu. Yu. Samitov, Z. I. Zelikman, A. I. Shkrebets, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 2, 319 (1974).Google Scholar
  13. 13.
    Yu. Yu. Samitov, Atlas of the Nuclear Magnetic Resonance Spectra of Spatial Isomers [in Russian], Vol. 1, Izd. Kazansk Gos. Univ., Kazan (1978), pp. 84, 85.Google Scholar
  14. 14.
    D. S. Eflax and A. P. Dunlop, J. Org. Chem., 26, 2106 (1961).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • R. A. Karakhanov
    • 1
  • M. R. Skurko
    • 1
  • T. Yu. Solov'eva
    • 1
  • L. Yu. Brezhnev
    • 1
  • L. F. Lapuka
    • 1
  • M. M. Vartanyan
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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