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Unusual direction of the radical reaction of esters with ethylenic compounds

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Conclusions

  1. 1.

    A study was made of the addition reaction, initiated by peroxides, of diethyl malonate, dimethyl succinate and ethyl monochloroacetate to the polyhaloolefins — to hexafluoropropylene, trichloroethylene and tetrachloroethylene.

  2. 2.

    The reaction proceeds by an anomalous direction: the α-carbon atom of the alcohol portion of the ester molecule takes part either exclusively or predominantly in the formation of the new carbon — carbon bond of the adducts.

  3. 3.

    The reaction of esters with trichloro- and tetrachloroethylene is accompanied by the elimination of hydrogen chloride and leads to the respective formation of either the 1-(dichlorovinyl) or 1-(trichlorovinyl) derivatives of alkyl esters of carboxylic acids.

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Literature cited

  1. 1.

    M. S. Kharasch, W. H. Urry, and E. V. Jensen, J. Am. Chem. Soc.,67, 1626 (1945); A. D. Petrov, G. I. Nikishin, and Yu. N. Ogibin, Dokl. Akad. Nauk SSSR,131, 580 (1960); J. C. Allen, J. I G. Cadogan, B. W. Harris, and D. H. Hey, J. Chem. Soc., 4468 (1962); J. I. G. Cadogan, D. H. Hey, and J. T. Sharp, J. Chem. Soc., C, 1743 (1966); G. I. Nikishin, R. I. Mustafaev, and A. D. Petrov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 359 (1963); Yu. N. Ogibin and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 378 (1965); N. F. Cywinski and H. J. Hepp, J. Org. Chem.,30, 3814 (1965).

  2. 2.

    G. I. Nikishin, Yu. N. Ogibin, and A. D. Petrov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1326 (1961).

  3. 3.

    High Resolution NMR Spectra Catalog, Varian, Analytical Instrument Division, Palo Alto (1963).

  4. 4.

    G. I. Nikishin, M, I. Dyusenov, and G. V. Somov, Izv. Akad. Nauk SSSR, Ser. Khim., 2188 (1966).

  5. 5.

    A. M. Lovelace, D. A. Rausch, and W. Postelnek, Aliphatic Fluorine Compounds [Russian translation], IL (1961).

  6. 6.

    G. I. Nikishin, Yu. N. Ogibin, and I. A. Palanuer, Izv. Akad. Nauk SSSR, Ser. Khim., 2478 (1967).

  7. 7.

    Cheves Walling, Free Radicals in Solution [Russian translation], IL (1960), pp.215, 290.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1066–1072, May, 1971.

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Nikishin, G.I., Ogibin, Y.N. & Lebedev, V.N. Unusual direction of the radical reaction of esters with ethylenic compounds. Russ Chem Bull 20, 980–985 (1971). https://doi.org/10.1007/BF00862208

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Keywords

  • Succinate
  • Malonate
  • Trichloroethylene
  • Alkyl Ester
  • Tetrachloroethylene