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Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1446–1452 | Cite as

Quantum Chemical Study of Mechanisms of Organic Reactions: VII. Reaction of Ethane-1,2-dithiol with 1,3-Dichloropropene in the System Hydrazine Hydrate–KOH

  • E. A. ChirkinaEmail author
  • L. B. Krivdin
  • E. P. Levanova
  • N. A. Korchevin
  • I. B. Rozentsveig
Article
  • 14 Downloads

Abstract

A mechanism has been proposed for the reaction of 1,3-dichloropropene with ethane-1,2-dithiol in the system hydrazine hydrate–potassium hydroxide on the basis of DFT quantum chemical calculations [B3LYP/6-311++G(d,p)]. The proposed mechanism involves several consecutive steps, in particular nucleophilic substitution of chlorine at the sp3-hybridized carbon atom by sulfur, prototropic allylic rearrangement of the monosubstitution product with double bond migration toward the sulfur atom, dithiolane ring closure via nucleophilic attack of the second thiolate group on the carbon atom in the γ-position with respect to the second chlorine atom, and prototropic allylic rearrangement of 2-vinyl-1,3-dithiolane to more stable 2-ethylidene-1,3-dithiolane.

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • E. A. Chirkina
    • 1
    • 2
    Email author
  • L. B. Krivdin
    • 1
    • 2
  • E. P. Levanova
    • 1
  • N. A. Korchevin
    • 1
    • 2
  • I. B. Rozentsveig
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia
  2. 2.Angarsk State Technical UniversityAngarsk, Irkutsk oblastRussia

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