Abstract
A study was carried out on the electrophilic substitution reactions of benzene and toluene by the action of a mixture of an acyl halide and benzaldehyde in the presence of trivalent lanthanide salts LnCl3, where Ln=Ce, Dy, Er, Sm, Yb, and Yb(O3SCF3)3, as catalysts at 40‡C over 24 h. The reaction stops at the formation of the corresponding triarylmethane compounds. A mechanism was proposed for this reaction. Lanthanide salts were found not to catalyze the usual Friedel-Crafts acylation of arenes.
Literature cited
G. Klopman, J. Am. Chem. Soc.,90, 223 (1968).
R. G. Parr and R. G. Pearson, J. Am. Chem. Soc.,105, 7512 (1983).
G. A. Olah, S. Kobayashy, and M. Tashiro, J. Am. Chem. Soc.,94, 7448 (1972).
N. Mine, J. Fujiwara, and H. Taniguchi, Chem. Lett., 357 (1986).
P. Bigler, H. Muhle, and M. Neuenschwander, Synthesis, 593 (1978).
J. Kutscher and A. Schneider, Inorg. Nucl. Chem. Lett.,7, 81 (1971).
J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, et al., J. Org. Chem.,52, 1017 (1987).
H. Gilman and J. E. Kirby, J. Am. Chem. Soc.,28, 1733 (1926).
H. Herrig and M. Schliffer, Ann.,422, 328 (1923).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 708–710, March, 1990.
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Davydov, D.V., Vinogradov, S.A. & Beletskaya, I.P. Catalytic activity of trivalent lanthanide salts in the alkylation reactions of aromatic hydrocarbons by the action of a mixture of an acyl halide and benzaldehyde. Russ Chem Bull 39, 629–630 (1990). https://doi.org/10.1007/BF00959603
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DOI: https://doi.org/10.1007/BF00959603