Conclusions
-
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.
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.
Similar content being viewed by others
Literature cited
M. J. Perkins, Free Radicals (ed. J. K. Koch) Vol. 2, New York-London-Sydney-Toronto, Wiley-Interscience (1973), p. 231.
D. C. Nonhebel and J. C. Walton, Free-Radical Chemistry, Cambridge Univ. Press (1973).
H. J. M.Dou, G. Vernin, and J. Metzger, Bull. Soc. Chim. France, 4593 (1971).
M. G. Vinogradov, S. P. Verenchikov, T. M. Fedorova, and G. I. Nikishin, J. Org. Khim.,11, 947 (1975).
H. Finkbeiner and J. B. Bush, Disc. Faraday Soc., No. 46, 150 (1968).
R. E. Ploeg, R. W. Korte, and E. C. Kooyman, J.Catal.,10, 52 (1968).
E. I. Heiba, R. M. Dessau, and W. J. Koehl, J. Am. Chem. Soc.,91, 138 (1969).
R. A. McClelland, R. O. C. Norman, and C. B. Thomas, J. Chem. Soc., Perkin Trans. 1, 562 (1972).
Y. Ogata, T. Itoh, and Y. Izawa, Bull. Chem. Soc. Jpn.,42, 794 (1969).
M. E. Kurz and T. Y. R. Chen, Chem. Commun., 968 (1976).
B. R. Cowley, R. O. C. Norman, and W. A. Waters, J. Chem. Soc., 1799 (1959).
W. A. Pryor, W. H. Davis, and J. H. Gleaton, J. Org. Chem.,40, 2099 (1975).
F. Minisci and O. Porta, Advances in Heterocyclic Chemistry, Vol. 16, Academic Press, N.Y.-L (1974), p. 150.
R. S. Min and V. S. Aksenov, Khim. Geterotsikl. Soedin., 224 (1976).
Ya. L. Gol'dfarb, G. P. Pokhil, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR,167, 823 (1966).
G. Brauer (editor), Handbuch der Präparativen Anorganisches Chemie [Russian translation], IL (1956), pp. 217, 672.
Organic Syntheses [Russian translation], No. 7, IL (1956), p. 44.
R. Cagniant, Bull. Soc. Chim. France, 847 (1949).
I. Houben-Weyl, Methoden der Organischen Chemie [Russian translation], Vol. 2, Goskhimizdat (1963), p. 515.
J. N. Chatterjca, C. Bakhta, and R. Radna-Vakula, J. Indian Chem. Soc.,49, 1161 (1972).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2292–2295, October, 1979.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00947563