Abstract
It is shown that the trifluoroacetylation of 9-methylcarbazole proceeds regio-specifically in the 3 position of the ring. 1,1,1-Tris(9-methyl-3-carbazolyl)-2,2,2-trifluoroethane and 1,1,1′,1′-tetrakis(9-methyl-3-carbazolyl)-2,2,2,2′,2′,-2′-hexafluorodiethyl ether were also isolated from the reaction mixture. Bis(trifluoroacetyl) derivatives were not detected. Only a 3-trifluoroacetyl derivative is formed when the reaction is carried out by heating in the presence of pyridine.
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A. Cipiciani, S. Clementi, P. Linda, G. Savelli, and G. V. Sebastiani, Tetrahedron, 32, 2595 (1976).
A. S. Bailey, J. B. Hoxby, A. N. Hilton, J. M. Peach, and M. H. Vandrevala, J. Chem. Soc. Perkin Trans. I, No. 2, 382 (1981).
J. Kahovec and Popišil, Collect. Czech. Chem. Commun., No. 33, 1709 (1969).
W. D. Kray and R. W. Rosser, J. Org. Chem., 42., 1186 (1977).
A. R. Katritzky and J. M. Lagowsky, Principles of Heterocyclic Chemistry, Academic Press (1968).
I. L. Knunyants, Chen-Ching-Yan, and N. P. Gambaryan, Zh. Vses. Khim. Ova., 5, 114 (1960).
N. P. Gambaryan, E. M. Rokhlin, Yu. V. Zeifman, Cheng-Ching-Yan, and I. L. Knuyants, Angew. Chem., 5, 947 (1966).
N. P. Buu-Hoi and R. Royer, J. Org. Chem., No. 15, 123 (1950).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 640–642, May, 1984.
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Sirotkina, E.E., Moskalev, N.V. & Shabotkin, I.G. Trifluoroacetylation of 9-methylcarbazole. Example of the formation of a triarylfluoroethane in the heterocyclic series. Chem Heterocycl Compd 20, 512–514 (1984). https://doi.org/10.1007/BF00514303
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DOI: https://doi.org/10.1007/BF00514303