Acetylferrocene is the
organoiron compound with the formula (C
5H
5)Fe(C
5H
4COCH
3). It consists of
ferrocene
Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...
substituted by an
acetyl group
In organic chemistry, an acetyl group is a functional group denoted by the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl grou ...
on one of the
cyclopentadienyl Cyclopentadienyl can refer to
* Cyclopentadienyl anion, or cyclopentadienide,
** Cyclopentadienyl ligand
* Cyclopentadienyl radical, •
* Cyclopentadienyl cation,
See also
* Pentadienyl
{{Chemistry index ...
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
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...
(Ac
2O):
:Fe(C
5H
5)
2 + Ac
2O → (C
5H
5)Fe(C
5H
4Ac) + 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 (C
5H
5)Fe(C
5H
4CH(OH)Me) and precursor to
vinylferrocene. The oxidized derivative, acetyl
ferrocenium, is used as a 1e-oxidant in the research laboratory.
References
External links
*{{Commons category-inline
Ferrocenes
Cyclopentadienyl complexes
Acetyl compounds