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Reactions of fluoro olefins

Communication 17. Competing conjugation in perfluoroalkenylphosphonic esters

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  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.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences, USSR

    I. L. Knunyants, E. Ya. Pervova & V. V. Tyuleneva

Authors
  1. I. L. Knunyants
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  2. E. Ya. Pervova
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  3. V. V. Tyuleneva
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Knunyants, I.L., Pervova, E.Y. & Tyuleneva, V.V. Reactions of fluoro olefins. Russ Chem Bull 12, 1439–1444 (1963). https://doi.org/10.1007/BF00844090

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  • DOI: https://doi.org/10.1007/BF00844090

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