(Benzylideneacetone)iron tricarbonyl

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(Benzylideneacetone)iron tricarbonyl
(benzylideneacetone)iron-tricarbonyl-2D-skeletal.png
(benzylideneacetone)iron-tricarbonyl-3D-balls.png
Identifiers
Properties
C13H10FeO4
Molar mass 286.060
Appearance Red solid
Melting point 88 to 89 °C (190 to 192 °F; 361 to 362 K)
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

(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.

Synthesis, reactions, related reagents[edit]

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[edit]

  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. ^ A. J. P. Domingos, J. A. S. Howell, B. F. G. Johnson, J. Lewis (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

Additional reading[edit]

  • 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.