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Homolytic oxoalkylation of furan, α-methylfuran, and thiophene

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

Conclusions

  1. 1.

    Homolytic substitution in the heteroaromatic ring of furan,α-methylfuran, and thiophene by CH3COCH2 and CH3 COCHCOCH3 radicals generated from acetone and acetylacetone using Mn(III) acetate (a one-electron oxidizing agent) proceeds regiospecifically at theα-carbon atom of the ring and leads to 2-furyl- and 2-thienyl ketones.

  2. 2.

    Acetoxylation and C-C or C-O dehydrodimerization occurs in the oxidation of 2-furyl- and 2-thienyl ketones by Mn(III) acetate. The reaction pathway depends on the concentration of Mn(OAc)3.

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Authors and Affiliations

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

    R. S. Min, V. S. Aksenov, M. G. Vinogradov & G. I. Nikishin

  2. Institute of Petroleum Chemistry, Siberian Branch of the Academy of Sciences of the USSR, Tomsk

    R. S. Min, V. S. Aksenov, M. G. Vinogradov & G. I. Nikishin

Authors
  1. R. S. Min
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  2. V. S. Aksenov
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  3. M. G. Vinogradov
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  4. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2315–2320, October, 1981.

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Min, R.S., Aksenov, V.S., Vinogradov, M.G. et al. Homolytic oxoalkylation of furan, α-methylfuran, and thiophene. Russ Chem Bull 30, 1902–1907 (1981). https://doi.org/10.1007/BF00963420

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  • DOI: https://doi.org/10.1007/BF00963420

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