(Benzylideneacetone)iron tricarbonyl

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CASNo = 38333-35-6
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Formula = C₁₃H₁₀FeO₄
MolarMass = 286.060
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MeltingPt = 88 - 89 °C
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The organometallic compound (benzylideneacetone)iron tricarbonyl is a widely employed reagent for transferring the Fe(CO)₃ unit to other organic molecules. [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.] This red-colored compound is commonly abbreviated (bda)Fe(CO)₃. It is prepared by the reaction of Fe₂(CO)₉ with benzylideneacetone, typically in refluxing ethoxyethane. [Alcock, N. W.; Richards, C. J.; Thomas, S. E. ”Preparation of Tricarbonyl(ε⁴-vinylketene)iron(0) Complexes from Tricarbonyl(ε⁴-vinyl ketone)iron(0) Complexes and Their Subsequent Conversion to Tricarbonyl(ε⁴-vinylketenimine)iron(0) Complexes” "Organometallics" 1991, volume 10, pp 231 - 238.doi|10.1021/om00047a054.] The identity and purity of the compound can be determined by its IR spectrum: it absorbs strongly at 2065, 2005, 1985 cm⁻¹, in cyclohexane solution.

Related Fe(CO)₃ transfer agents

A popular source of Fe(CO)₃ is the simplest, 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, form conveniently reactive Fe(CO)₃ adducts, which have been shown to be superior in some ways to (bda)Fe(CO)₃. [ 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.]

(bda)Fe(CO)₃ reacts with Lewis bases to give adducts without displacement of the bda. [Howell, J. A. S.; Kola, J. C.; Dixon, D. T.; Burkinshaw, P. M. and Thomas, M. J., "The kinetics and mechanism of diene exchange in (É≈4-enone) Fe(CO)2L complexes (L = phosphine, phosphite)", Journal of Organometallic Chemistry, 1984, 266, 83-96]

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