Russian Chemical Bulletin

, Volume 49, Issue 9, pp 1575–1582 | Cite as

New approach to cyclic sulfites and sulfates through reactions of sulfur oxychlorides with glycidols

  • A. A. Bredikhin
  • A. v. Pashagin
  • Z. A. Bredikhina
  • S. N. Lazarev
  • A. T. Gabaidullin
  • I. A. Litvinov
Organic Chemistry


Reactions of 2,3-epoxyalcohols (glycidols) with thionyl chloride or sulfuryl chloride afford cyclic sulfites or sulfates, respectively. These reactions yield predominantly 4-chloroalkyl-1,3,2-dioxathiolane oxides. The configuration of the C(4) atom in the latter compounds exactly corresponds to that of the C(2) atom of the parent glycidol, whereas the configuration of the exocyclic atom is almost completely reversed with respect to that of the C(3) atom of the precursor.

Key words

epoxyalcohols thionyl chloride sulfuryl chloride cyclic sulfites cyclic sulfates stereochemistry 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    W. Baker and F. B. Field,J. Chem. Soc., 1932, 86.Google Scholar
  2. 2.
    Y. Gao and K. B. Sharpless,J. Am. Chem. Soc., 1988,110, 7538.CrossRefGoogle Scholar
  3. 3.(a)
    B. B. Lohray,Synthesis, 1992, 1035; (b) H. C. Kolb, M. S. Van Nieuwenhze, and K. B. Sharpless,Chem. Rev., 1994,94, 2483; (c) B. B. Lohray and V. Bhushan,Adv. Heterocyclic Chem., 1997,68, 89.Google Scholar
  4. 4.(a)
    A. A. Bredikhin, S. N. Lazarev, Z. A. Bredikhina, and V. A. Al'fonsov,Phosph., Sulf., Silicon, 1997,131, 173; (b) A. A. Bredikhin, S. N. Lazarev, and Z. A. Bredikhina,Zh. Obshch. Khim., 1997,67, 1806 [Russ. J. Gen. Chem., 1997,67, (Engl. Transl.)]; (c) A. A. Bredikhin and S. N. Lazarev,Mendeleev Commun., 1998,8, 81; (d) A. A. Bredikhin, A. V. Pashagin, E. I. Strunskaya, A. T. Gubaidullin, I. A. Litvinov, and Z. A. Bredikhina,Izv. Akad. Nauk. Ser. Khim., 1999, 2110 [Russ. Chem. Bull., 1999,48, 2086 (Engl. Transl.)].Google Scholar
  5. 5.
    A. A. Bredikhin, S. N. Lazarev, A. V. Pashagin, and Z. A. Bredikhina,Mendeleev Commun., 1999,9, 236.CrossRefGoogle Scholar
  6. 6.
    J. P. Vigneron, M. Dhaenens, and A. Horeau,Tetrahedron, 1973,29, 1055.CrossRefGoogle Scholar
  7. 7.
    P. Maroni, L. Cazaux, G. Chassaing, I. Preizner, and T. le Trang,Bull. Soc. Chim. Fr., Part II, 1975, 1258.Google Scholar
  8. 8.
    J. -P. Gorrichon, G. Chassing, and L. Cazaux,Org. Magn. Reson., 1983,21, 426.CrossRefGoogle Scholar
  9. 9.
    C. H. Green and D. G. Hellier,J. Chem. Soc., Perkin Trans. 2, 1975, 190.Google Scholar
  10. 10.
    G. W. Buchanan and D. G. Hellier,Can. J. Chem., 1976,54, 1428.CrossRefGoogle Scholar
  11. 11.
    N. Kasai, T. Suzuki, and Y. Furukawa,J. Mol. Catal., B: Enzymatic, 1998,4, 237.CrossRefGoogle Scholar
  12. 12.(a)
    J. J. Baldwin, A. W. Raab, K. Mensler, B. H. Arison and D. E. McClure,J. Org. Chem., 1978,43, 4876; (b) Y. Kawakami, T. Asai, K. Umeyama, and Y. Yamashita,J. Org. Chem., 1982,47, 3581; (c) M. K. Ellis, B. T. Golding, A. B. Maude, and W. P. Watson,J. Chem. Soc., Perkin Trans. 1, 1991, 747.CrossRefGoogle Scholar
  13. 13.(a)
    T. Katsuki and V. S. Martin,Org. Rect., 1996,48, 1; (b) R. A. Johnson and K. B. Sharpless, inCatalytic Asymmetric Synthesis, Ed. I. Ojima, I VCH, New York, 1993, 103.Google Scholar
  14. 14.
    Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless,J. Am. Chem. Soc., 1987,109, 5765.CrossRefGoogle Scholar
  15. 15.
    S. Takano, M. Yanase, and K. Ogasewara,Heterocycles, 1989,29, 249.CrossRefGoogle Scholar
  16. 16.
    C. H. Green and D. G. Hellier,J. Chem. Soc., Perkin Trans. 2, 1973, 243.Google Scholar
  17. 17.
    A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo,Acta Crystallogr., Sect. A, 1991,47, 744.CrossRefGoogle Scholar
  18. 18.
    W. C. Hamilton,Acta Crystallogr., 1965,18, 502.CrossRefGoogle Scholar
  19. 19.
    L. H. Straver and A. J. Schierbeek,MolEN. Structure Determination System, Nonius B. V., 1994, No. 1, 2.Google Scholar
  20. 20.
    A. L. Spek,Acta Crystallogr., Sect. A, 1990,46, C34.Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 2000

Authors and Affiliations

  • A. A. Bredikhin
    • 1
  • A. v. Pashagin
    • 1
  • Z. A. Bredikhina
    • 1
  • S. N. Lazarev
    • 1
  • A. T. Gabaidullin
    • 1
  • I. A. Litvinov
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryKazan Research Center of the Russian Academy of SciencesKazanRussian Federation

Personalised recommendations