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Radical addition of polyhalomethanes to polychloroolefins in the presence of nucleophilic solvents

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

Conclusions

  1. 1.

    In the interaction of 5,5,5-trichloro-1-pentene and 4,4,4-trichloro-1-butene with polyhalomethanes in the presence of tert-butylperoxide in isopropanol or diethyl ether solution, together with the “normal” adducts with structure CCl3(CH2)nCHXCH2CCl3, where X=Br or Cl, compounds with the structure CCl3 ·(CH2)nCH2CH2CCl3 are formed. The formation of the latter is explained by the fact that at the step of chain transfer, the intermediately formed electrophilic radicals with the structure CCl3(CH2)nĊHCH2CCl3 enter into a competitive reaction with the nucleophilic solvent.

  2. 2.

    The homolytic interaction of 3,3,3-trichloropropene with CCl4 in the presence of solvents leads to the formation of compounds with the structure CHCl2CHClCH2CCl3 and CCl2=CHCH2CCl3 as a result of rearrangement of the intermediate radical CCl3CHCH2CCl3 to the radical CCl2CHClCH2CCl3. The latter reacts partially with the solvent and is stabilized chiefly by the elimination of atomic chlorine.

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Authors and Affiliations

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

    I. A. Shvarts, M. Ya. Khorlina & R. Kh. Freidlina

Authors
  1. I. A. Shvarts
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  2. M. Ya. Khorlina
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  3. R. Kh. Freidlina
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Additional information

The article is published on the basis of a resolution of the Conference of Editors-in-Chief of Journals of the Academy of Sciences of the USSR from June 12, 1962, as the dissertation work of I. A. Shvarts.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2018–2023, September, 1970.

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Shvarts, I.A., Khorlina, M.Y. & Freidlina, R.K. Radical addition of polyhalomethanes to polychloroolefins in the presence of nucleophilic solvents. Russ Chem Bull 19, 1897–1901 (1970). https://doi.org/10.1007/BF00849768

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  • DOI: https://doi.org/10.1007/BF00849768

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