Russian Chemical Bulletin

, Volume 46, Issue 6, pp 1181–1183 | Cite as

Comparison of α- and β-trifluoromethylsubstituted acrylic acids in their reactions with thiols

  • T. P. Vasil'eva
  • A. F. Kolomiets
  • E. I. Mysov
  • A. V. Fokin
Brief Communications

Abstract

α-(Trifluoromethyl)acrylic acid (1) and γ,γ,γ-trifluorocrotonic acid (2) add AcSH (exothermally and at 100 °C, respectively) in the absence of a catalyst to form products of β-thiolation, which can be easily hydrolyzed to the corresponding β-mercaptoalkanoic acids. Thiols also add regiospecifically to acids1 (in the absence of a catalyst) and2 only in the presence of trifluoromethanesulfonic acid as the catalyst) when heated.

Key words

α-(trifluoromethyl)acrylic acid, γ,γ,γ-trifluorocrotonic acid, thiolacetic acid thiols, thiolation 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. Kitazume, T. Ikeya, and K. Murata,Chem. Commun., 1986, 1331.Google Scholar
  2. 2.
    T. Kitazume and K. Murata,J. Fluor. Chem., 1987,36, 339.CrossRefGoogle Scholar
  3. 3.
    P. Bevilacqua, D. Keith, and J. Roberts,J. Org. Chem., 1984,49, 1430.CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • T. P. Vasil'eva
    • 1
  • A. F. Kolomiets
    • 1
  • E. I. Mysov
    • 1
  • A. V. Fokin
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations