Reactions of fluoro olefins

Communication 17. Competing conjugation in perfluoroalkenylphosphonic esters
  • I. L. Knunyants
  • E. Ya. Pervova
  • V. V. Tyuleneva
Organic and Biological Chemistry


  1. 1.

    In competition for conjugation with an olefinic bond the phosphono group has a mote powerful electronwithdrawing effect than the trifluoromethyl group. The reaction of diethyl perfluoropropenylphosphonate with various nucleophilic reagents leads to products in which a fluorine atom in theβ -position relative to the phosphono group is replaced.

  2. 2.

    It was found that the electron-withdrawing effect of two trifluoromethyl groups is more powerful than the effect due to one phosphono group: in the reaction of diethyl perfluoroisobutenylphosphonate with nucleophilic reagents it is theα-fluorine atom that is replaced; in the case of diethyl α-hydrohexafluoroisobutenylphosphonate, addition products are formed with nucleophilic reagents, i.e. α-substituted-α, β-dihydrohexafluoroisobutylphosphonic esters.



Ester Diethyl Fluorine Trifluoromethyl Fluoro 
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Copyright information

© Consultants Bureau 1964

Authors and Affiliations

  • I. L. Knunyants
    • 1
  • E. Ya. Pervova
    • 1
  • V. V. Tyuleneva
    • 1
  1. 1.Institute of Heteroorganic CompoundsAcademy of SciencesUSSR

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