(Benzylideneacetone)iron tricarbonyl

(Benzylideneacetone)iron tricarbonyl
Identifiers
CAS number 38333-35-6
Properties
Molecular formula C13H10FeO4
Molar mass 286.060
Melting point

88 - 89 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The organometallic compound (benzylideneacetone)iron tricarbonyl is a widely employed reagent for transferring the Fe(CO)3 unit to other organic molecules.[1] 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 diethyl ether.[2] The identity and purity of the compound can be determined by its IR spectrum: it absorbs strongly at 2065, 2005, and 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.[3]

(bda)Fe(CO)3 reacts with Lewis bases to give adducts without displacement of the bda.[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. ^ 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.
  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.
  4. ^ Howell, J. A. S.; Kola, J. C.; Dixon, D. T.; Burkinshaw, P. M. and Thomas, M. J. (1984). "The kinetics and mechanism of diene exchange in (É≈4-enone) Fe(CO)2L complexes (L = phosphine, phosphite)". Journal of Organometallic Chemistry 266: 83–96. doi:10.1016/0022-328X(84)80113-8.