View PDF Version
 
DOI: 10.1039/A806708B (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 63-66

1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel–Crafts acylation reactions of ferrocene

(Note: The full text of this document is currently only available in the PDF Version )

Annegret Stark, Bonnie L. MacLean and Robert D. Singer

Abstract

Friedel–Crafts acylations of ferrocene in 1-ethyl-3-methylimidazolium halogenoaluminate ionic liquids, [emim]I–(AlCl3)x are described.3 The effect of varying the “bulk” Lewis acidity of the ionic liquids used as solvents in these reactions and the effect of varying the relative amounts of acylating agent with respect to the amount of ferrocene in these reactions is also described. The use of a variety of different acylating agents in our studies demonstrates the scope of this reaction performed in these ionic liquid systems.

References

  1. V. R. Koch, L. L. Miller and R. A. Osteryoung, J. Am. Chem. Soc., 1976, 98, 5277 CrossRef CAS.
  2. J. Boon, J. Levisky, J. Pflug and J. S. Wilkes, J. Org. Chem., 1986, 51, 480 CrossRef CAS.
  3. J. K. D. Surette, L. Green and R. D. Singer, Chem. Commun., 1996, 2753 RSC.
  4. R. T. Carlin and J. S. Wilkes, J. Mol. Catal., 1990, 63, 125 CrossRef CAS.
  5. P. J. Dyson, M. C. Grossel, N. Srinivasan, T. Vine, T. Welton, D. J. Williams, A. J. P. White and T. Zigras, J. Chem. Soc., Dalton Trans., 1997, 3465 RSC.
  6. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser and R. D. Rogers, Chem. Commun., 1998, 1765 RSC.
  7. J. S. Wilkes, J. A. Levisky, R. A. Wilson and C. L. Hussey, Inorg. Chem., 1982, 21, 1263 CrossRef CAS.
  8. A. A. Fannin, L. A. King, J. A. Levisky and J. S. Wilkes, J. Phys. Chem., 1984, 88, 2609 CrossRef; R. J. Gale, B. Gilbert and R. A. Osteryoung, Inorg. Chem., 1978, 2728 CrossRef CAS; R. J. Gray and G. E. Maciel, J. Am. Chem. Soc., 1981, 103, 71; T. Matsumoto and K. J. Ichikawa, J. Am. Chem Soc., 1984, 106, 43; J. S. Wilkes, J. S. Frye and G. F. Reynolds, Inorg. Chem., 1983, 22, 3870 CrossRef CAS.
  9. R. B. Woodward, M. Rosenblum and M. C. Whiting, J. Am. Chem. Soc., 1952, 74, 3458 CrossRef CAS; M. Rosenblum, J. O. Santer and W. G. Howells, J. Am. Chem. Soc., 1963, 85, 1450 CrossRef CAS.
  10. G. Lemay, S. Kaliaguine, A. Adnot, S. Nahar, D. Cozak and J. Monnier, Can. J. Chem., 1986, 64, 1943 CAS.
  11. B. Chevrier and R. Weiss, Angew. Chem., Int. Ed. Engl., 1974, 13, 1 CrossRef.
  12. L. Schwink and P. Knochel, Chem. Eur. J., 1998, 4, 950 CrossRef CAS and references therein.
  13. A. A. Sada, A. M. Greenway, P. B. Hitchcock, T. J. Mohammed, K. R. Seddon and J. A. Zora, J. Chem. Soc., Chem. Commun., 1986, 1753 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.