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Chemistry of Heterocyclic Compounds

, Volume 18, Issue 10, pp 1032–1036 | Cite as

Sigmatropic rearrangements of alkenyl benzofuryl and benzothienyl sulfides

  • A. V. Anisimov
  • V. S. Babaitsev
  • T. A. Kolosova
  • E. A. Viktorova
Article

Abstract

The thio Claisen rearrangement of 2-butenyl 2-benzofuryl sulfide, cyclopenten-2-yl 2-benzofuryl sulfide, 2-butenyl 2-benzothienyl sulfide, and cyclopenten-2-yl 2-benzothienyl sulfide was investigated. The rates, energies and entropies of activation of the process were calculated, and the effect of the structure of the sulfide, the polarity of the solvent, and the temperature was demonstrated by comparison of these values. The 1,3-thioallyl rearrangement of 1-methylallyl 3-methyl-2-benzothienyl sulfide was studied, and it was shown that this reaction competes with the thio Claisen rearrangement.

Keywords

Entropy Sulfide Organic Chemistry Thio Sigmatropic Rearrangement 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • A. V. Anisimov
    • 1
  • V. S. Babaitsev
    • 1
  • T. A. Kolosova
    • 1
  • E. A. Viktorova
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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