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Reactions of perfluorome thacrylic acid derivatives with hydroxy and mercapto compounds

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

Conclusions

  1. 1.

    Perfluoromethacrylic acid derivatives (methyl ester and dimethylamide) easily add carboxylic acids at the C=C bond to give comparatively stableα-hydro-β-acyloxypentafluoroisobutyric acid derivatives. These adducts when heated are cleaved to the corresponding acyl fluoride andα-hydro-α-fluorocarbonyltrifluoropropionic acid derivative.

  2. 2.

    Hydrogen chloride adds to the perfluoromethacrylic acid dimethylamide to give theα-hydro-β-chloropentafluoroisobutyric acid derivative. The perfluoromethacrylic acid ester reacts in a similar manner only in the presence of a base.

  3. 3.

    The perfluoromethacrylic acid dimethylamide when reacted with phenol, thiophenol, and benzyl mercaptan gives the substitution products of the vinyl fluorine atom (mixture of cis and trans isomers), while with pentafluorophenol it gives a mixture of substitution and addition products.

  4. 4.

    The reaction rate of the perfluoromethacrylic acid dimethylamide with nucleophiles decreases in the order: RCOOH > AlkOH > C6H5SH > C6F5OH > C6H5CH2SH > C6H5OH ≫ (CF3)2CHOH.

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Literature cited

  1. Yu. A. Cheburkov and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1573 (1963).

  2. D. C. England, L. Salomon, and C. G. Krespan, J. Fluorine Chem.,3, 63 (1973).

    Google Scholar 

  3. E. G. Abduganiev, É. A. Avetisyan, E. M. Rokhlin, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim, 392 (1974).

  4. J. Houben-Weyl, Methoden der organischen Chemie, Berlin (1972), 5/1b, p.946.

  5. R. D. Chambers and R. G. Mobbs, in: Fluorine in Organic Chemistry, Wiley-Interscience (1973).

  6. Yu. A. Cheburkov, N. Mukhamadaliev, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1476 (1965).

  7. I. L. Knunyants, M. P. Krasuskaya, and N. P. Gambaryan, Izv. Akad. Nauk SSSR, Ser. Khim., 723 (1965).

  8. J. Matier and A. Allet, Principles of Organic Synthesis [Russian translation], IL (1962), p.586.

  9. Syntheses of Organic Fluorine Compounds [in Russian], Khimiya (1973), p.182.

  10. I. L. Knunyants and B. L. Dyatkin, Izv. Akad. Nauk SSSR, Ser. Khim., 923 (1964).

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Authors and Affiliations

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

    U. Utebaev, E. M. Rokhlin & É. P. Lur'e

Authors
  1. U. Utebaev
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  2. E. M. Rokhlin
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  3. É. P. Lur'e
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.142–148, January, 1976.

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Utebaev, U., Rokhlin, E.M. & Lur'e, É.P. Reactions of perfluorome thacrylic acid derivatives with hydroxy and mercapto compounds. Russ Chem Bull 25, 129–134 (1976). https://doi.org/10.1007/BF00925634

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  • DOI: https://doi.org/10.1007/BF00925634

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