(Benzylideneacetone)iron tricarbonyl
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • [Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].O=C(\C=C\c1ccccc1)C
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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(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.

Structure and bonding

(bda)Fe(CO)3 is an example of a complex of an η2-ketone. It is a piano stool complex. The compound is characterized by IR bands at 2065, 2005, and 1985 cm−1 (cyclohexane solution), the three bands being indicative of the low symmetry of the complex, which is chiral.

Synthesis, reactions, related reagents

Crystals of (Benzylidenacetone)iron tricarbonyl

It is prepared by the reaction of Fe2(CO)9 with benzylideneacetone.[2]

(bda)Fe(CO)3 sometimes reacts with Lewis bases to give adducts without displacement of the bda.[3] The reagents of the type (bda)Fe(CO)2(PR3) function as sources of "Fe(CO)2(PR3)" (R = aryl, etc.).[4]

Other sources of Fe(CO)3 are Fe2(CO)9 and Fe(CO)3(cyclooctene)2. The latter is highly reactive and thermally sensitive. Imine derivatives of cinnamaldehyde, e.g. C6H5CH=CHC(H)=NC6H5, also form reactive Fe(CO)3 adducts, which have been shown to be superior in some ways to (bda)Fe(CO)3.[5]

References

  1. ^ Knölker, Hans-Joachim (2001-04-15). "(η4-Benzylideneacetone)tricarbonyliron". In John Wiley & Sons, Ltd (ed.). (η 4 -Benzylideneacetone)tricarbonyliron. Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/047084289x.rb058. ISBN 978-0-471-93623-7.
  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 Tricarbonyliron and Tricarbonylruthenium". Inorg. Synth. Inorganic Syntheses. Vol. 28. pp. 52–55. doi:10.1002/9780470132593.ch11. ISBN 9780470132593.
  3. ^ A.S. Howell, James; Kola, John C.; Dixon, Denis T.; Burkinshaw, Philip M.; Thomas, Marion J. (1984). "The kinetics and mechanism of diene exchange in (η4-enone) Fe(CO)2L complexes (L = phosphine, phosphite)". Journal of Organometallic Chemistry. 266 (1): 83–96. doi:10.1016/0022-328X(84)80113-8.
  4. ^ Johnson, Brian F. G.; Lewis, Jack; Stephenson, G. Richard; Vichi, Eduardo J. S. (1978). "Preparation and reactions of triphenylphosphine and triphenyl phosphite complexes of (benzylideneacetone)dicarbonyliron(0)". Journal of the Chemical Society, Dalton Transactions (5): 369–373. doi:10.1039/dt9780000369. ISSN 0300-9246.
  5. ^ Knölker, Hans-Joachim; Braier, Arnold; Bröcher, Dirk J.; Cämmerer, Simon; Fröhner, Wolfgang; Gonser, Peter; Hermann, Holger; Herzberg, Daniela; Reddy, Kethiri R.; Rohde, Guy (2001-07-01). "Recent applications of tricarbonyliron-diene complexes to organic synthesis". Pure and Applied Chemistry. 73 (7): 1075–1086. doi:10.1351/pac200173071075. ISSN 1365-3075. S2CID 98692646.

Further reading

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