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1,5-Migration of hydrogen in intermediate polychloroalkyl radicals formed by the reaction of 1,1,1,3-tetrachloro-propane with vinylidene chloride

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

Conclusions

  1. 1.

    The reaction of 1,1,1,3-tetrachloropropane with vinylidene chloride, initiated by Fe(CO)5 in combination with nucleophilic cocatalysts, yields telomer homologs, ClCH2CH2CCl2-(CH2CCl2)nCl. A telomer with n=1 was isolated.

  2. 2.

    Aside from the telomer homologs, hexachloropentane, CHCl2CH2CCl2CH2CHCl2 and pentachloropentane CH2ClCH2CCl2CH2CHCl2, are formed in this reaction. It is proposed that the hexachloropentane results from a 1,5 H migration in the intermediate radical ClCH2CH2CCl2CH2CCl2, and the pentachloropentane from the removal of a hydrogen atom from the solvent by the same radical.

  3. 3.

    The properties of two radicals, ClCH2CH2CCl2CH2ĊCl2 and ClCH2CH2CCl2CH2CH2 were compared under equivalent conditions, and it was shown that the tendency for 1,5 hydrogen migration to occur is inherent in alkyldichloromethyl radicals.

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Literature cited

  1. R. Kh. Freidlina, in: G. H. Williams, ed., Advances in Free Radical Chemistry, Academic Press, New York (1965), pp. 324–325, 248.

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  2. L. M. Bobinova, E. N. Zil'berman, B. L. Zvezdin, I. Ya. Slonim, and O. A. Mochalova, Zh. Org. Khim.,5, 216 (1969).

    Google Scholar 

  3. R. Kh. Freidlina, and E. C. Chukovakaya, Synthesis, 447, 485, 483, 478 (1974).

  4. N. V. Kruglova, Sh. A. Karapetyan, and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 1569 (1975).

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Authors and Affiliations

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

    N. A. Kuz'mina, E. Ts. Chukovskaya & R. Kh. Freidlina

Authors
  1. N. A. Kuz'mina
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  2. E. Ts. Chukovskaya
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  3. R. Kh. Freidlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 847–850, April, 1977.

The authors thanks V. I. Dostovalov for taking the NMR spectra and for participating in the discussions.

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Kuz'mina, N.A., Chukovskaya, E.T. & Freidlina, R.K. 1,5-Migration of hydrogen in intermediate polychloroalkyl radicals formed by the reaction of 1,1,1,3-tetrachloro-propane with vinylidene chloride. Russ Chem Bull 26, 771–774 (1977). https://doi.org/10.1007/BF01108198

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  • DOI: https://doi.org/10.1007/BF01108198

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