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Acetylferrocene

| NFPA-H = 4 | NFPA-F = 1 | NFPA-R = 0 50 mg kg−1 (oral, mouse)

Acetylferrocene is the organoiron compound with the formula (C5H5)Fe(C5H4COCH3). It consists of ferrocene substituted by an acetyl group on one of the cyclopentadienyl rings. It is an orange, air-stable solid that is soluble in organic solvents.

Preparation and reactions

Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac2O): :Fe(C5H5)2 + Ac2O → (C5H5)Fe(C5H4Ac) + HOAc

The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.

Acetylferrocene can be converted to many derivatives, e.g., reduction to the chiral alcohol (C5H5)Fe(C5H4CH(OH)Me) and precursor to vinylferrocene. The oxidized derivative, acetylferrocenium, is used as a 1e-oxidant in the research laboratory.

References

References

  1. "Brief Guide to Inorganic Nomenclature".
  2. {{Sigma-Aldrich. Aldrich
  3. http://msds.chem.ox.ac.uk/AC/acetylferrocene.html {{Dead link. (August 2022)
  4. Bozak, R. E. "Acetylation of ferrocene: A chromatography experiment for elementary organic laboratory" J. Chem. Educ., 1966, volume 43, p 73.{{doi. 10.1021/ed043p73
  5. Donahue, C. J., Donahue, E. R., "Beyond Acetylferrocene: The Synthesis and NMR Spectra of a Series of Alkanoylferrocene Derivatives", Journal of Chemical Education 2013, volume 90, pp. 1688. {{doi. 10.1021/ed300544n
  6. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews.
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ferrocenes cyclopentadienyl-complexes acetyl-compounds
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