Chemistry of Heterocyclic Compounds

, Volume 17, Issue 9, pp 876–879 | Cite as

Synthesis and three-dimensional structure of 5,5-disubstituted 2-alkoxy-1,3-dioxanes

  • L. F. Lapuka
  • O. B. Chalova
  • E. A. Kantor
  • T. K. Kiladze
  • D. L. Rakhmankulov


It was established by PMR spectroscopy that a chair conformation with an axial orientation of the alkoxy substituent is the primary conformation for 5,5-disubstituted (and unsubstituted) 2-alkoxy-1,3-dioxanes. As compared with alkyl-1,3-dioxanes, 2-alkoxy-1,3-dioxanes are characterized by reversal of the chemical shifts of the axial and equatorial protons attached to C4, and C6.


Spectroscopy Organic Chemistry Chemical Shift Dioxane Axial Orientation 
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Literature cited

  1. 1.
    E. L. Eliel and C. A. Giza, J. Org. Chem., 33, 3754 (1968).Google Scholar
  2. 2.
    E. L. Eliel and F. W. Nader, J. Am. Chem. Soc., 92, 584 (1970).Google Scholar
  3. 3.
    E. L. Eliel and F. W. Nader, J. Am. Chem. Soc., 92, 3045 (1970).Google Scholar
  4. 4.
    F. W. Nader and E. L. Eliel, J. Am. Chem. Soc., 92, 3050 (1970).Google Scholar
  5. 5.
    N. S. Zefirov and N. M. Shekhtman, Usp. Khim., 40, 593 (1971).Google Scholar
  6. 6.
    S. L. Zhdanov, in: Modern Problems of Organic Chemistry [in Russian], Vol. 5, Izd. Leningradsk. Gos. Univ., Leningrad (1976), p. 2.Google Scholar
  7. 7.
    N. S. Zefirov and I. V. Kazimirchik, Usp. Khim., 43, 252 (1974).Google Scholar
  8. 8.
    M. Anteunis, D. Tavernier, and F. Borremans, Heterocycles, 4, 293 (1976).Google Scholar
  9. 9.
    Yu. Yu. Samitov, Khim. Geterotsikl. Soedin., No. 12, 1587 (1978).Google Scholar
  10. 10.
    A. I. Gren', S. G. Soboleva, and G. R. Tantsyura, in: Problems in Stereochemistry [in Russian], Vysshaya Shkola, Kiev (1971), p. 52.Google Scholar
  11. 11.
    G. Stoddart, The Stereochemistry of Carbohydrates [Russian translation], Mir, Moscow (1975), p. 183.Google Scholar
  12. 12.
    G. Kh. Kamai, N. A. Chadaeva, I. I. Saidashev, and N. K. Tazeeva, in: Problems in Stereochemistry [in Russian], Vol. 1, Izd. Kievsk. Univ., Kiev (1971), p. 127.Google Scholar
  13. 13.
    B. A. Arbuzov and Yu. Yu. Samitov, Tetrahedron Lett., No. 8, 433 (1963).Google Scholar
  14. 14.
    Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR, 164, 347 (1965).Google Scholar
  15. 15.
    J. B. Lambert, J. Am. Chem. Soc., 89, 1836 (1967).Google Scholar
  16. 16.
    O. B. Chalova, E. A. Kantor, R. A. Karakhanov, and D. L. Rakhmankulov, Public Scientific-Research Institute of Theoretical and Experimental Chemistry, Cherkassy, No. 192khp-D-80 (February 14, 1980); Ref. Zh. Khim., 22ZW65 (1980).Google Scholar
  17. 17.
    S. M. McElvain and Y. W. Nelson, J. Am. Chem. Soc., 64, 1825 (1942).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • L. F. Lapuka
    • 1
  • O. B. Chalova
    • 1
  • E. A. Kantor
    • 1
  • T. K. Kiladze
    • 1
  • D. L. Rakhmankulov
    • 1
  1. 1.Ufa Petroleum InstituteUfa

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