Hydrolysis of fluoroalkyl-containing Β-aminovinyl ketones

  • L. N. Bazhenova
  • V. I. Filyakova
  • V. E. Kirichenko
  • K. I. Pashkevich
Organic Chemistry

Abstract

The kinetics of hydrolysis of fluoroalkyl-containing Β-aminovinyl ketones R1C(O)CHC(NHR3)R2, in which the substituents CF3 and HCF2CF2 are in the ketone (R1) or enamine parts of the molecule (R2), was studied. In acid (pH < 5) and alkaline (pH > 10) media, they hydrolyze with the formation of the corresponding amines and Β-diketones. In an alkaline medium, the Β-diketones undergo cleavage to fluorinated acids and methyl ketones. The rate constants of hydrolysis in an acid medium change within a range of four orders, depending on the nature of the substituents. The presence of a fluoroalkyl group at the enamine reaction center increases the hydrolysis rate. In an alkaline medium, the rate constants vary within one order.

Keywords

Methyl Hydrolysis Ketone Reaction Center Acid Medium 

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • L. N. Bazhenova
    • 1
  • V. I. Filyakova
    • 1
  • V. E. Kirichenko
    • 1
  • K. I. Pashkevich
    • 1
  1. 1.Department of Fine Organic Synthesis, Institute of Chemistry, Bashkir Scientific Center, Urals BranchAcademy of Sciences of the USSRSverdlovsk

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