(Benzylideneacetone)iron tricarbonyl

Chemical compound From Wikipedia, the free encyclopedia

(Benzylideneacetone)iron tricarbonyl is the organoiron compound with the formula (C6H5CH=CHC(O)CH3)Fe(CO)3. It is a reagent for transferring the Fe(CO)3 unit.[1] This red-colored compound is commonly abbreviated (bda)Fe(CO)3.

Quick facts Identifiers, Properties ...
(Benzylideneacetone)iron tricarbonyl
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C10H10O.3CO.Fe/c1-9(11)7-8-10-5-3-2-4-6-10;3*1-2;/h2-8H,1H3;;;;/b8-7+;;;;
    Key: BVYZFTVCCNDAIM-YZNHWISSSA-N
  • [Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].O=C(\C=C\c1ccccc1)C
Properties
C13H10FeO4
Molar mass 286.060
Appearance Red solid
Melting point 88 to 89 Â°C (190 to 192 Â°F; 361 to 362 K)
slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Structure and bonding

(bda)Fe(CO)3 is an example of a complex of an η2-ketone. It is a piano stool complex. The compound is characterized by IR bands at 2065, 2005, and 1985 cm−1 (cyclohexane solution), the three bands being indicative of the low symmetry of the complex, which is chiral.

Synthesis, reactions, related reagents

Crystals of (Benzylideneacetone)iron tricarbonyl

It is prepared by the reaction of Fe2(CO)9 with benzylideneacetone.[2]

(bda)Fe(CO)3 sometimes reacts with Lewis bases to give adducts without displacement of the bda.[3] The reagents of the type (bda)Fe(CO)2(PR3) function as sources of "Fe(CO)2(PR3)" (R = aryl, etc.).[4]

Other sources of Fe(CO)3 are Fe2(CO)9 and Fe(CO)3(cyclooctene)2. The latter is highly reactive and thermally sensitive. Imine derivatives of cinnamaldehyde, e.g. C6H5CH=CHC(H)=NC6H5, also form reactive Fe(CO)3 adducts, which have been shown to be superior in some ways to (bda)Fe(CO)3.[5]

References

Further reading

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