Conclusions
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1.
Oxidative chlorination of alkanonitriles CH3(CH2)nCN (n=2–6) with sodium persulfate in the presence of an equimolar quantity of copper chloride in water and in hydrochloric acid occurred at each carbon atom of the alkyl chain with the exception of theα position.
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2.
On reaction in water the relative content of an individual chloroalkanonitrile in the mixture of isomers increased depending on the extent of removal of the radical center from the CN group in the intermediate cyanoalkyl radicals, reaching a maximum on substitution at the (ω-1)-th carbon atom.
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3.
On reaction in hydrochloric acid 5-chloroalkanonitriles were formed predominantly which indicated the intramolecular participation of the cyano group in the generation of the intermediate 4-cyanoalkyl radicals.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2316–2322, October, 1983.
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Troyanskii, É.I., Svitan'ko, I.V., Ogibin, Y.N. et al. Oxidative chlorination of alkanonitriles in the system Na2S2O8-CuCl2 . Russ Chem Bull 32, 2090–2094 (1983). https://doi.org/10.1007/BF00955778
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DOI: https://doi.org/10.1007/BF00955778