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Radical reaction of acetone with aromatic compounds

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

Conclusions

  1. 1.

    Anisole, toluene, chlorobenzene, ethyl benzoate, and benzonitrile have been substituted in the aromatic nucleus by the CH3COCH2 radical, generated in the redox system acetone-Mn(OAc)3-AcOH at 70°. The acetonyl radical displays electrophilic properties in this reaction.

  2. 2.

    The radical reaction of acetone with thiophene proceeds selectively at the α-carbon atom of the thiophene ring to form 1-(2-thienyl)propan-2-one.

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Literature cited

  1. M. J. Perkins, Free Radicals (ed. J. K. Koch) Vol. 2, New York-London-Sydney-Toronto, Wiley-Interscience (1973), p. 231.

    Google Scholar 

  2. D. C. Nonhebel and J. C. Walton, Free-Radical Chemistry, Cambridge Univ. Press (1973).

  3. H. J. M.Dou, G. Vernin, and J. Metzger, Bull. Soc. Chim. France, 4593 (1971).

  4. M. G. Vinogradov, S. P. Verenchikov, T. M. Fedorova, and G. I. Nikishin, J. Org. Khim.,11, 947 (1975).

    Google Scholar 

  5. H. Finkbeiner and J. B. Bush, Disc. Faraday Soc., No. 46, 150 (1968).

    Google Scholar 

  6. R. E. Ploeg, R. W. Korte, and E. C. Kooyman, J.Catal.,10, 52 (1968).

    Google Scholar 

  7. E. I. Heiba, R. M. Dessau, and W. J. Koehl, J. Am. Chem. Soc.,91, 138 (1969).

    Google Scholar 

  8. R. A. McClelland, R. O. C. Norman, and C. B. Thomas, J. Chem. Soc., Perkin Trans. 1, 562 (1972).

    Google Scholar 

  9. Y. Ogata, T. Itoh, and Y. Izawa, Bull. Chem. Soc. Jpn.,42, 794 (1969).

    Google Scholar 

  10. M. E. Kurz and T. Y. R. Chen, Chem. Commun., 968 (1976).

  11. B. R. Cowley, R. O. C. Norman, and W. A. Waters, J. Chem. Soc., 1799 (1959).

  12. W. A. Pryor, W. H. Davis, and J. H. Gleaton, J. Org. Chem.,40, 2099 (1975).

    Google Scholar 

  13. F. Minisci and O. Porta, Advances in Heterocyclic Chemistry, Vol. 16, Academic Press, N.Y.-L (1974), p. 150.

    Google Scholar 

  14. R. S. Min and V. S. Aksenov, Khim. Geterotsikl. Soedin., 224 (1976).

  15. Ya. L. Gol'dfarb, G. P. Pokhil, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR,167, 823 (1966).

    Google Scholar 

  16. G. Brauer (editor), Handbuch der Präparativen Anorganisches Chemie [Russian translation], IL (1956), pp. 217, 672.

  17. Organic Syntheses [Russian translation], No. 7, IL (1956), p. 44.

  18. R. Cagniant, Bull. Soc. Chim. France, 847 (1949).

  19. I. Houben-Weyl, Methoden der Organischen Chemie [Russian translation], Vol. 2, Goskhimizdat (1963), p. 515.

  20. J. N. Chatterjca, C. Bakhta, and R. Radna-Vakula, J. Indian Chem. Soc.,49, 1161 (1972).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2292–2295, October, 1979.

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Min, R.S., Aksenov, V.S., Vinogradov, M.G. et al. Radical reaction of acetone with aromatic compounds. Russ Chem Bull 28, 2114–2117 (1979). https://doi.org/10.1007/BF00947563

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  • DOI: https://doi.org/10.1007/BF00947563

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