(Benzylideneacetone)iron tricarbonyl is the

organoiron compound Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrat ...

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 colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohe ...

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 Benzylideneacetone is the organic compound described by the formula C6H5CH=CHC(O)CH3. Although both ''cis''- and ''trans''-isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed. Its original preparation demons ...

. (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 spe ...

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(C9H8O) C6H5CH=CHCHO. 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 shi ...

, e.g. CHCH=CHC(H)=NCH, also form reactive Fe(CO)

adduct An adduct (from the Latin ''adductus'', "drawn toward" 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 co ...

s, which have been shown to be superior in some ways to (bda)Fe(CO).

Structure and bonding

Synthesis, reactions, related reagents

References

Further reading