Russian Journal of Organic Chemistry

, Volume 44, Issue 1, pp 31–37 | Cite as

Quantum-chemical study on the mechanism of formation of geminal hydroxy thiols by reaction of 1,3-dihalopropan-2-ones with hydrogen sulfide

  • V. A. Shagun
  • L. G. Shagun
  • I. A. Dorofeev
  • I. A. Mikhailova
  • M. G. Voronkov
Article

Abstract

The reaction mechanism of 1,3-dihalopropan-2-ones with hydrogen sulfide in the presence of hydrogen chloride was studied in terms of the density functional theory. Unlike 1-halopropan-2-ones which give rise to 1-halo-2-sulfanylpropan-2-ols via preliminary enolization, 1,3-dihalopropan-2-ones preferentially undergo direct nucleophilic attack on the carbonyl group by hydrogen sulfide. The potential energy surface for rotational isomerism of 1,3-dihalopropane-2-thiones and 1,3-dihalo-2-sulfanylpropan-2-ols was analyzed, and their most stable rotamers were identified.

Keywords

Potential Energy Surface Hydrogen Sulfide Halogen Atom Enol Form Hydrogen Chloride 

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Copyright information

© Pleiades Publishing, Ltd. 2008

Authors and Affiliations

  • V. A. Shagun
    • 1
  • L. G. Shagun
    • 1
  • I. A. Dorofeev
    • 1
  • I. A. Mikhailova
    • 1
  • M. G. Voronkov
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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