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Action of nucleophilic reagents on compounds of the type [Cl(CH2)nCCl=]2

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

Summary

  1. 1.

    By the hydrogenation of 1,1,1,9-tetrachlorononane over palladium, 1.9,9,10,10,18-hexachlorooctadecane was synthesized. Under the action of zinc this hexachloro compound gave 1,9,10,18-tetrachloro-9-octadecene.

  2. 2.

    Reaction of nucleophilic reagents with compounds of the type [Cl (CH2)n CCl =]2 gave the compounds X(CH2)nCCl=CCl(CH2)nCl (n=2,4, and 8) and X(CH2)n CCl=CCl(CH2)n X(n=4,6) X=CH3COO, OH, (C2H5)2N, CN, COOH, (C2H5)3.NI.

  3. 3.

    1,3,4,6-Tetrachloro-3-hexene, unlike the saturated 1,3,3,4,4,6-hexachlorohexane and 1,1,1,3-tetrachloropropane, undergoes exchange reactions with nucleophilic reagents, but these reactions proceed less readily than those with higher tetrachloroalkenes.

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Literature cited

  1. British Patent 652,768; Chem. Abs.46, 1577c (1952).

  2. A. N. Nesmeyanov, L. I. Zakharkin, and T. A. Kost, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 657 (1955).

  3. A. N. Nesmeyanov, R. Kh. Freidlina, L. I. Zakharkin, and T. A. Kost, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 211 (1960).

  4. R. Kh. Freidlina and T. A. Kost, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 644 (1957).

  5. V. A. Nekrasov, Doklady Akad. Nauk SSSR88, 73 (1953).

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Authors and Affiliations

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

    R. Kh. Freidlina & T. A. Kost

Authors
  1. R. Kh. Freidlina
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  2. T. A. Kost
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Freidlina, R.K., Kost, T.A. Action of nucleophilic reagents on compounds of the type [Cl(CH2)nCCl=]2 . Russ Chem Bull 9, 1291–1293 (1960). https://doi.org/10.1007/BF00907657

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  • DOI: https://doi.org/10.1007/BF00907657

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