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Direct oxidation of alkanoic acids to lactones

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    By the action of the Na2S2O8-CuCl2 system, alkanoic acids RR′CHCH(R″)CH2COOH convert into γ-lactones

    with high regioselectivity.

  2. 2.

    A reaction mechanism was proposed, including the formation from alkanoic acids of alkylcarbonyloxyl radicals, their rearrangement with 1,5-migration of the H atom into 3-carboxylalkyl radicals, and oxidative cyclization of the latter into γ-lactones.

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Authors and Affiliations

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

    É. I. Troyanskii, I. V. Svitan'ko & G. I. Nikishin

Authors
  1. É. I. Troyanskii
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  2. I. V. Svitan'ko
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  3. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2318–2325, October, 1982.

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Troyanskii, É.I., Svitan'ko, I.V. & Nikishin, G.I. Direct oxidation of alkanoic acids to lactones. Russ Chem Bull 31, 2041–2046 (1982). https://doi.org/10.1007/BF00950650

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  • DOI: https://doi.org/10.1007/BF00950650

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