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

  • D. V. Davydov
  • S. A. Vinogradov
  • I. P. Beletskaya
Brief Communications
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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.

Keywords

Benzene Toluene Hydrocarbon Catalytic Activity Aromatic Hydrocarbon 

Literature cited

  1. 1.
    G. Klopman, J. Am. Chem. Soc.,90, 223 (1968).Google Scholar
  2. 2.
    R. G. Parr and R. G. Pearson, J. Am. Chem. Soc.,105, 7512 (1983).Google Scholar
  3. 3.
    G. A. Olah, S. Kobayashy, and M. Tashiro, J. Am. Chem. Soc.,94, 7448 (1972).Google Scholar
  4. 4.
    N. Mine, J. Fujiwara, and H. Taniguchi, Chem. Lett., 357 (1986).Google Scholar
  5. 5.
    P. Bigler, H. Muhle, and M. Neuenschwander, Synthesis, 593 (1978).Google Scholar
  6. 6.
    J. Kutscher and A. Schneider, Inorg. Nucl. Chem. Lett.,7, 81 (1971).Google Scholar
  7. 7.
    J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, et al., J. Org. Chem.,52, 1017 (1987).Google Scholar
  8. 8.
    H. Gilman and J. E. Kirby, J. Am. Chem. Soc.,28, 1733 (1926).Google Scholar
  9. 9.
    H. Herrig and M. Schliffer, Ann.,422, 328 (1923).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • D. V. Davydov
    • 1
  • S. A. Vinogradov
    • 1
  • I. P. Beletskaya
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR

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