Cyclopentadienone

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Cyclopentadienone
Cyclopentadienone.svg
Names
Preferred IUPAC name
Cyclopenta-2,4-dien-1-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5H4O/c6-5-3-1-2-4-5/h1-4H
    Key: FQQOMPOPYZIROF-UHFFFAOYSA-N
  • InChI=1/C5H4O/c6-5-3-1-2-4-5/h1-4H
    Key: FQQOMPOPYZIROF-UHFFFAOYAD
  • C1=CC(=O)C=C1
Properties
C5H4O
Molar mass 80.086 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclopentadienone is an organic compound with molecular formula C5H4O. The parent cyclopentadienone is rarely encountered, because it rapidly dimerizes. [1] Many substituted derivatives are known, notably tetraphenylcyclopentadienone. Such compounds are used as ligands in organometallic chemistry. [2]

Contents

The Knolker complex, derived from a substituted cyclopentadienone, is a catalyst for transfer hydrogenation. KloelkerCmpx.png
The Knölker complex, derived from a substituted cyclopentadienone, is a catalyst for transfer hydrogenation.

Preparation

Cyclopentadienone can be generated by the photolysis or pyrolysis of various substances (e.g. 1,2-benzoquinone [4] ), and then isolated in an argon matrix at 10 K (−263 °C). It dimerizes readily upon thawing the matrix at 38 K (−235 °C). [5] [6]

See also

Related Research Articles

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H
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)
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. The molecule consists of two cyclopentadienyl rings bound on opposite sides of a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation Fe(C
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H
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)+
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Cyclopentadienyliron dicarbonyl dimer Chemical compound

Cyclopentadienyliron dicarbonyl dimer is an organometallic compound with the formula [(η5-C5H5)Fe(CO)2]2, often abbreviated to Cp2Fe2(CO)4, [CpFe(CO)2]2 or even Fp2, with the colloquial name "fip dimer". It is a dark reddish-purple crystalline solid, which is readily soluble in moderately polar organic solvents such as chloroform and pyridine, but less soluble in carbon tetrachloride and carbon disulfide. Cp2Fe2(CO)4 is insoluble in but stable toward water. Cp2Fe2(CO)4 is reasonably stable to storage under air and serves as a convenient starting material for accessing other Fp (CpFe(CO)2) derivatives (described below).

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References

  1. Ogliaruso, Michael A.; Romanelli, Michael G.; Becker, Ernest I. (1965). "Chemistry of Cyclopentadienones". Chemical Reviews. 65: 261–367. doi:10.1021/cr60235a001.
  2. Quintard, A.; Rodriguez, J. (2014). "Iron Cyclopentadienone Complexes: Discovery, Properties, and Catalytic Reactivity". Angewandte Chemie International Edition. 53: 4044–4055. doi:10.1002/anie.201310788.
  3. Casey, Charles P.; Guan, Hairong (2007). "An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones". Journal of the American Chemical Society. 129 (18): 5816–5817. doi:10.1021/ja071159f. PMID   17439131.
  4. Brown, Roger F. C. (2012). Pyrolytic Methods in Organic Chemistry: Application of Flow and Flash Vacuum Techniques. Elsevier. p. 173. ISBN   978-0-323-15417-8.
  5. Maier, Günther; Franz, Lothar Hermann; Hartan, Hans-Georg; Lanz, Klaus; Reisenauer, Hans Peter (1985). "Kleine Ringe. 54. Cyclopentadienon" [Small rings. 54. Cyclopentadienone]. Chemische Berichte (in German). 118 (8): 3196–3204. doi:10.1002/cber.19851180819.
  6. Horspool, William M.; Lenci, Francesco. CRC Handbook of Organic Photochemistry and Photobiology. 1–2 (2nd ed.). p. 12-8. ISBN   978-0-203-49590-2.