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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

Abstract

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 

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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

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