Acetylferrocene

 ( Ferrocenes ) 

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.

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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.Bozak, R. E. "Acetylation of ferrocene: A chromatography experiment for elementary organic laboratory" J. Chem. Educ., 1966, volume 43, p 73.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.

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.

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