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Formation of bicyclic adducts in the reactions of fluorinated 2,4-cyclohexadien-1-ones with 2-carboxyhenzenediazonium

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Benzyne generated during the decomposition of 2-carboxybenzenediazonium interacts with 6-chloro-2,3,4,5,6-pentafluoro-2,4-cyclohexadien-1-one, 6-chloro-2,4,5,6-tetrafluoro-3-methoxy-2,4-cyclohexadien-1-one, 6-chloro-2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-2,4-cyclohexadien-1-one, and perfluoro-6-phenoxy-2,4-cyclohexadien-1-one to form [4+2]-cycloaddition products. The latter are easily converted to 1-naphthylacetic acid derivatives by the action of O- and N-nucleophiles.

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References

  1. L. S. Kobrina and V. D. Shteingarts,Zh. Org. Khim., 1988,24, 1344 [J. Org. Chem. USSR, 1988,24, 1211 (Engl. Transl.)]; L. S. Kobrina and A. A. Bogachev,J. Fluor. Chem., 1993,62, 243.

    Google Scholar 

  2. D. Del Mazza and M. C. Reinecke,J. Org. Chem., 1988,53, 5799.

    Google Scholar 

  3. L. Friedman and F. M. Logullo,J. Am. Chem. Soc., 1963,85, 1549.

    Google Scholar 

  4. A. C. G. Gray and H. Hart,J. Am. Chem. Soc., 1968,90, 2569.

    Google Scholar 

  5. L. S. Kobrina and V. D. Shteingarts,J. Fluor. Chem., 1988,41, 111.

    Google Scholar 

  6. R. W. Hoffmann, inDehydrobenzene and Cycloalkynes, Academic Press, New York, 1967, 99.

    Google Scholar 

  7. I. F. Mikhailova and V. A. Barkhash.Zh. Org. Khim., 1970,6, 2325 [J. Org. Chem. USSR, 1970,6 (Engl. Transl.)]

    Google Scholar 

  8. H. Hart and A. Oku,J. Org. Chem., 1972,37, 4969.

    Google Scholar 

  9. A. Oku and A. Matsui,Bull. Chem. Soc. Jpn., 1977,50, 3338.

    Google Scholar 

  10. N. E. Akhmetova, A. A. Shtark, and V. D. Shteingarts,Zh. Org. Khim., 1973,9, 1218 [J. Org. Chem. USSR, 1973,9 (Engl. Transl.)]

    Google Scholar 

  11. N. E. Akhmetova, N. G. Kostina, and V. D. Shteingarts,Zh. Org. Khim., 1979.15, 2137 [J. Org. Chem. USSR, 1979,15 (Engl. Transl.)]

    Google Scholar 

  12. L. S. Kobrina, V. N. Kovtonyuk, and G. G. Yakobson.Zh. Org. Khim., 1977,13, 1447 [J. Org. Chem. USSR, 1977,13 (Engl. Transl.)]

    Google Scholar 

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

    A. A. Bogachev, L. S. Kobrina & V. D. Shteingarts

Authors
  1. A. A. Bogachev
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  2. L. S. Kobrina
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  3. V. D. Shteingarts
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1634–1637, September, 1994.

This work was carried out with the financial support of the International Science Foundation (Project No. Ch2-6713-0925).

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Bogachev, A.A., Kobrina, L.S. & Shteingarts, V.D. Formation of bicyclic adducts in the reactions of fluorinated 2,4-cyclohexadien-1-ones with 2-carboxyhenzenediazonium. Russ Chem Bull 43, 1546–1549 (1994). https://doi.org/10.1007/BF00697146

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  • DOI: https://doi.org/10.1007/BF00697146

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