Cyclopentadienone Explained

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] thumb|left|The Knölker complex, derived from a substituted cyclopentadienone, is a catalyst for transfer hydrogenation.^[3]

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 . It dimerizes readily upon thawing the matrix at .^{[5] [6]}

See also

• Dienone

Notes and References

1. Michael A.. Ogliaruso. Michael G.. Romanelli. Ernest I.. Becker. Chemistry of Cyclopentadienones. Chemical Reviews. 1965. 65. 261–367. 10.1021/cr60235a001.
2. Quintard. A.. Rodriguez. J.. Iron Cyclopentadienone Complexes: Discovery, Properties, and Catalytic Reactivity. Angewandte Chemie International Edition. 2014. 53. 4044–4055. 10.1002/anie.201310788.
3. 10.1021/ja071159f. 17439131. An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones. Journal of the American Chemical Society. 129. 18. 5816–5817. 2007. Casey. Charles P.. Guan. Hairong.
4. Book: Brown, Roger F. C.. Pyrolytic Methods in Organic Chemistry: Application of Flow and Flash Vacuum Techniques. Elsevier. 2012. 978-0-323-15417-8. 173.
5. Maier. Günther. Franz. Lothar Hermann. Hartan. Hans-Georg. Lanz. Klaus. Reisenauer. Hans Peter. Kleine Ringe. 54. Cyclopentadienon. Small rings. 54. Cyclopentadienone. Chemische Berichte. 1985. 118. 8. 3196–3204. 10.1002/cber.19851180819. de.
6. Book: Horspool, William M.. Lenci. Francesco. CRC Handbook of Organic Photochemistry and Photobiology. 1–2. 2nd. 128. 978-0-203-49590-2.