Summary
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1.
A study was made of the action of nucleophilic reagents (KI, KOCOCH3 and NaCN) on hexachloroalkanes of structure [Cl(CH2)nCCl2-]2, in which n = 2, 4, and 6. It was found that hexachlorohexane is inert toward nucleophilic reagents. Hexachlorodecane and hexachlorotetradecane undergo substitution reactions at the chlorines of the chloromethyl groups under the action of nucleophilic reagents.
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The following compounds were prepared: [I(CH2)4CCl2-]2; [I(CH2)6CCL2; [CH3CO2(CH2)4CCl2]2; [HO(CH2)4CCl2-]2 [NC(CH2)4CCl2-]2; [NC(CH2)6CCl2-]2; [HO2C(CH2)6CCl2-]2; Cl(CH2)4CCl2-CCl2 (CH2)4OCOCH2; Cl(CH2)6CCl2-CCl2(CH2)6I.
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Literature
A. N. Nesmeyanov, R. Kh. Freidlina and L. I. Zakharkin, Proc. Acad. Sci. USSR 96, 87 (1954).
R. Kh. Freidlina and N. A. Semenov, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1957, 466.
British Pat. 652768; C. A. 46, 1577 (1952).
A. N. Nesmeyanov, L. I. Zakharkin and T. A. Kost, Bull. Acad. Sci. USSR, Diva Chem. Sci. 1955, 657.
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Freidlina, R.K., Kost, T.A. Action of nucleophilic reagents on compounds of the type [Cl(CH2)nCCl2-]2 . Russ Chem Bull 6, 656–658 (1957). https://doi.org/10.1007/BF01169287
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DOI: https://doi.org/10.1007/BF01169287