Russian Chemical Bulletin

, Volume 44, Issue 10, pp 1914–1916 | Cite as

Phase-transfer catalysis in reactions of 5-alkyl-3H-furan-2-ones with dichlorocarbene

  • V. A. Sedavkina
  • V. A. Morozova
  • A. Yu. Egorova
  • R. G. Savkin
Organic Chemistry
  • 19 Downloads

Abstract

Treatment of 5-alkyl-3H-furan-2-ones and 5-alkyl-3H-thiophen-2-ones with dichlorocarbene under conditions of phase-transfer catalysis at 20–90 °C results in insertion of the carbene at the C=C bond followed by skeletal rearrangement.

Key words

5-alkyl-3H-furan-2-ones 5-alkyl-3H-thiophen-2-ones 6-alkyl-5-chloropyran-2-ones 6-alkyl-5-oxohydropyran-2-ones 1-alkyl-6,6-dichloro-2-oxabicyclo[3.1.0]hexan-3-ones dichlorocarbene phase-transfer catalysis 

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References

  1. 1.
    N. S. Zefirov, I. V. Kazimirchik, and K. A. Lukin,Tsikloprisoedinenie dikhlorkarbena k olefinam [Cycloaddition of Dichlorocarbene to Olefins], Nauka, Moscow, 1985, 152 pp. (in Russian).Google Scholar
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    A. A. Avetisyan and M. T. Dangyan,Usp. Khim., 1977, 1250 [Russ. Chem. Rev., 1977 (Engl. Transl.)].Google Scholar
  3. 3.
    V. A. Sedavkina, N. A. Morozova, A. Yu. Egorova, and I. G. Ostroumov,Khim. Geterotsikl. Soedin., 1987, 451 [Chem. Heterocycl. Compd., 1987 (Engl. Transl.)].Google Scholar

Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • V. A. Sedavkina
    • 1
  • V. A. Morozova
    • 1
  • A. Yu. Egorova
    • 1
  • R. G. Savkin
    • 1
  1. 1.N. G. Chenyshevskii Saratov State UniversitySaratovRussian Federation

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