Cyclopentadienone

Cyclopentadienone
Names
	Preferred IUPAC name Cyclopenta-2,4-dien-1-one
Identifiers
CAS Number	13177-38-3;
3D model (JSmol)	Interactive image;
ChemSpider	122931;
PubChem CID	139405;
CompTox Dashboard (EPA)	DTXSID80157203 ;
	InChI 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;
	SMILES C1=CC(=O)C=C1;
Properties
Chemical formula	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]

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 10 K (−263 °C). It dimerizes readily upon thawing the matrix at 38 K (−235 °C).^[5]^[6]

References

^ 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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[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. Vol. 1–2 (2nd ed.). p. 12-8. ISBN 978-0-203-49590-2.

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Preparation

See also

References