88 - 89 °C
|Except where noted otherwise, data are given for|
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
The organometallic compound (benzylideneacetone)iron tricarbonyl is a widely employed reagent for transferring the Fe(CO)3 unit to other organic molecules. 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. 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. "(η4-Benzylideneacetone)tricarbonyliron" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
- 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.
- 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.
- 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