Cyclopentadienone

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]

The Knölker complex, derived from a substituted cyclopentadienone, is a catalyst for transfer hydrogenation.[3]
Cyclopentadienone
Identifiers
3D model (JSmol)
ChemSpider
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

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. It dimerizes readily upon thawing the matrix (38 K).[5][6]

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See also

References
  1. Michael A. Ogliaruso, Michael G. Romanelli, Ernest I. Becker "Chemistry of Cyclopentadienones" Chem. Rev., 1965, vol. 65, pp 261–367. doi:10.1021/cr60235a001
  2. Quintard, A.; Rodriguez, J., "Iron Cyclopentadienone Complexes: Discovery, Properties, and Catalytic Reactivity", Angew. Chem. Int. Ed. 2014, vol. 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". Chem. Ber. (in German). 118 (8): 3196–3204. doi:10.1002/cber.19851180819.
  6. Horspool, William M.; Lenci, Francesco. CRC Handbook of Organic Photochemistry and Photobiology, Volumes 1 & 2 (2nd ed.). p. 12-8. ISBN 978-0-203-49590-2.
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