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Russian Journal of Organic Chemistry

, Volume 52, Issue 9, pp 1267–1276 | Cite as

Quantum chemical study of mechanisms of organic reactions: V. Addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile

  • E. A. Chirkina
  • A. G. Mal’kina
  • I. A. Ushakov
  • L. B. Krivdin
Article

Abstract

The mechanism of nucleophilic addition of ethane-1,2-dithiol to 4-hydroxy-4-methylpent-2-ynenitrile has been studied at the DFT B3LYP/6-311++G(d,p) level of theory. The base-catalyzed reaction involves nucleophilic attack by deprotonated ethane-1,2-dithiol on the ß-carbon atom of the nitrile with formation of intermediate Z-vinylic carbanion which undergoes intramolecular cyclization with closure of 1,3-dithiolane ring. Further transformation of 2-[2-(2-hydroxypropan-2-yl)-1,3-dithiolan-2-yl]acetonitrile to 6,6-dimethyl-7-oxo-1,4-dithiaspiro[4.4]nonan-8-imine has also been studied.

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Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • E. A. Chirkina
    • 1
  • A. G. Mal’kina
    • 1
  • I. A. Ushakov
    • 1
  • L. B. Krivdin
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian BranchRussian Academy of SciencesIrkutskRussia

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