Advertisement

Unsaturated acids containing a trifluoromethyl group

Communication 3. Polarization of the double bond in β-trifluoromethylcrotonic acid
  • I. L. Knunyants
  • Yu. A. Cheburkov
Article

Summary

  1. 1.

    β-Trifluoromethylcrotonic acid was obtained by the action of anhydrous sulfuric acid on β-trifluoromethyl-β-methylpropiolactone or β-trifluoromethyl-β-hydroxybutyric acid.

     
  2. 2.

    Thionyl chloride in distinction from phosphorus pentoxide easily dehydrates methyl β-trfluoromethyl-β-hydroxybutyrate.

     
  3. 3.

    After studying the direction of addition of methanol,ammonia, and ethanolamine to esters of β-trifluoromethylcrotonic acid it was concluded that the deciding role in the addition of nucleophilic reagents was played by polarization of the double bond, not steric hindrance.

     

Keywords

Methyl Chloride Methanol Ammonia Ester 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    H. Walborsky, M. Baum, and D. Loncrini, J. Amer. Chem. Soc.77, 3637 (1955).Google Scholar
  2. 2.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk1960, 678.Google Scholar
  3. 3.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk1960, 2168.Google Scholar
  4. 4.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk1961, No.5.Google Scholar
  5. 5.
    I. L. Knunyants, N. P. Gambaryan, and Cheng Ching-yün, Izv. AN SSSR, Otd. Khim. Nauk1960, 686.Google Scholar
  6. 8.
    T. Purdie and J. Irvin, J. Chem. Soc.75, 483 (1899).Google Scholar
  7. 7.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk 1961, No. 5.Google Scholar
  8. 8.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk1960, 2162.Google Scholar
  9. 9.
    I. L. Knunyants and Yu. A. Cheburkov, Izv. AN SSSR, Otd. Khim. Nauk1960, 1516.Google Scholar
  10. 10.
    H. Walborsky and M. Schwarz, J. Amer. Chem. Soc.75, 3241 (1953).Google Scholar

Copyright information

© Consultants Bureau 1961

Authors and Affiliations

  • I. L. Knunyants
    • 1
  • Yu. A. Cheburkov
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRUSSR

Personalised recommendations