French
DeutschCyclopentadienone
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| Names | |
|---|---|
| Preferred IUPAC name Cyclopenta-2,4-dien-1-one | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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| 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). | |
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]
Preparation
[edit]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
[edit]References
[edit]- ^ Ogliaruso, Michael A.; Romanelli, Michael G.; Becker, Ernest I. (1965). "Chemistry of Cyclopentadienones". Chemical Reviews. 65: 261–367. doi:10.1021/cr60235a001.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Horspool, William M.; Lenci, Francesco. CRC Handbook of Organic Photochemistry and Photobiology. Vol. 1–2 (2nd ed.). p. 12-8. ISBN 978-0-203-49590-2.
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