| Watchedfields | changed |
|---|---|
| Verifiedrevid | 454070258 |
| Iupacname | 1-Ferrocenylethan-1-one[1] |
| Othernames | Acetylferrocene |
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.[2][3]
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.[4]
References
- ^ "Brief Guide to Inorganic Nomenclature"
- ^ 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
- ^ 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
- ^ Connelly, Neil G. & Geiger, William E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774