(Benzylideneacetone)iron tricarbonyl

(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.

(Benzylideneacetone)iron tricarbonyl

Identifiers
CAS Number	38333-35-6^Y
InChI 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
Properties
Chemical formula	C13H10FeO4
Molar mass	286.060
Appearance	Red solid
Melting point	88 to 89 °C (190 to 192 °F; 361 to 362 K)
Solubility in water	slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Synthesis, reactions, related reagents

Crystals of (Benzylidenacetone)iron tricarbonyl

It is prepared by the reaction of Fe₂(CO)₉ with benzylideneacetone.[2] The compound is characterized by IR bands at 2065, 2005, and 1985 cm⁻¹ (cyclohexane solution).

(bda)Fe(CO)₃ reacts with Lewis bases to give adducts without displacement of the bda.[3]

Another popular source of Fe(CO)₃ is Fe₂(CO)₉. Alternatively, Fe(CO)₃(cyclooctene)₂ is highly reactive, the trade-off being that it is thermally sensitive. Imine derivatives of cinnamaldehyde, e.g. C₆H₅CH=CHC(H)=NC₆H₅, also form conveniently reactive Fe(CO)₃ adducts, which have been shown to be superior in some ways to (bda)Fe(CO)₃.[4]

References

1. Knölker, H.-J. "(η⁴-Benzylideneacetone)tricarbonyliron" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
2. Domingos, A. J. P.; Howell, J. A. S.; Johnson, B. F. G.; Lewis, J. (1990). "Reagents for the Synthesis of η-Diene Complexes of Tricarbonnyliron and Tricarbonylruthenium". Inorg. Synth. 28: 52–55. doi:10.1002/9780470132593.ch11.
3. Howell, J. A. S.; Kola, J. C.; Dixon, D. T.; Burkinshaw, P. M.; Thomas, M. J. (1984). "The kinetics and mechanism of diene exchange in (η⁴-enone)Fe(CO)2L complexes (L = phosphine, phosphite)". Journal of Organometallic Chemistry. 266: 83–96. doi:10.1016/0022-328X(84)80113-8.
4. Knölker, H.-J.; Braier, A.; Bröcher, D. J.; Cämmerer, S. Fröhner, W.; Gonser, P.; Hermann, H.; Herzberg, D.; Reddy, K. R.; Rohde, G. “Recent applications of tricarbonyliron-diene complexes to organic synthesis” Pure and Applied Chemistry 2001, Volume 73, pp. 1075–1086. doi:10.1351/pac200173071075

Further reading

• Alcock, N. W.; Richards, C. J.; Thomas, S. E. (1991). "Preparation of Tricarbonyl(η⁴-vinylketene)iron(0) Complexes from Tricarbonyl(ε⁴-vinyl ketone)iron(0) Complexes and Their Subsequent Conversion to Tricarbonyl(ε⁴-vinylketenimine)iron(0) Complexes". Organometallics. 10: 231–238. doi:10.1021/om00047a054.CS1 maint: uses authors parameter (link)