(Benzylideneacetone)iron tricarbonyl is the
organoiron compound with the formula (CHCH=CHC(O)CH)Fe(CO). It is a reagent for transferring the Fe(CO) unit. This red-colored compound is commonly abbreviated (bda)Fe(CO).
Structure and bonding
(bda)Fe(CO) is an example of a
complex of an η-ketone. It is a
piano stool complex
Half sandwich compounds, also known as piano stool complexes, are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples in ...
. The compound is characterized by
IR bands at 2065, 2005, and 1985
cm (
cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...
solution), the three bands being indicative of the low symmetry of the complex, which is chiral.
Synthesis, reactions, related reagents
It is prepared by the reaction of
Fe(CO) with
benzylideneacetone.
(bda)Fe(CO) sometimes reacts with
Lewis bases
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any s ...
to give adducts without displacement of the bda. The reagents of the type (bda)Fe(CO)(PR) function as sources of "Fe(CO)(PR)" (R = aryl, etc.).
Other sources of Fe(CO) are Fe(CO) and Fe(CO)(
cyclooctene). The latter is highly reactive and thermally sensitive.
Imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...
derivatives of
cinnamaldehyde
Cinnamaldehyde is an organic compound with the formula or . Occurring naturally as predominantly the ''trans'' (''E'') isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway ...
, e.g. CHCH=CHC(H)=NCH, also form reactive Fe(CO)
adduct
In chemistry, an adduct (; alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is ...
s, which have been shown to be superior in some ways to (bda)Fe(CO).
References
Further reading
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Organoiron compounds
Carbonyl complexes
Iron(0) compounds
Enones
Phenyl compounds
{{DEFAULTSORT:Benzylideneacetone, iron tricarbonyl