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Oxidation of acetoxyalkyl radicals by divalent copper salts

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

Conclusions

  1. 1.

    The 1-ethyl-3-aeetoxypropyl and 1-ethyl-4-acetoxybutyl radicals were respectively generated by the oxidative decarboxylation of the 2-ethyl-3-acetoxybutanoic and 2-ethyl-4-acetoxypentanoic acids under the influence of lead tetraacetate, and a study was made of their oxidation by the acetate, trifluoroacetate, fluoborate, sulfate, chloride and perchlorate of divalent copper.

  2. 2.

    Most of the copper salts oxidize the 1-ethyl-3-acetoxypropyl and 1-ethyl-4-acetoxybutyl radicals exclusively to the 2- and 3-pentenyl and the 3- and 4-hexenyl acetates, with the predominant formation of the isomers where the acetoxy group is furthest away from the double bond. Ligands that are coordinated with the copper are practically without effect on the ratio of the formed isomeric alkenyl acetates.

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Literature cited

  1. Yu. N. Ogibin, M. I. Katsin, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 573.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    M. I. Katsin, Yu. N. Ogibin & G. I. Nikishin

Authors
  1. M. I. Katsin
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  2. Yu. N. Ogibin
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  3. G. I. Nikishin
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Additional information

See [1] for previous communication.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 139–143, January, 1974.

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Katsin, M.I., Ogibin, Y.N. & Nikishin, G.I. Oxidation of acetoxyalkyl radicals by divalent copper salts. Russ Chem Bull 23, 129–133 (1974). https://doi.org/10.1007/BF00922327

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  • DOI: https://doi.org/10.1007/BF00922327

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