Cyclopentadienone

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

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References

Michael A. Ogliaruso, Michael G. Romanelli, Ernest I. Becker "Chemistry of Cyclopentadienones" Chem. Rev., 1965, vol. 65, pp 261–367. doi:10.1021/cr60235a001
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
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". Chem. Ber. (in German). 118 (8): 3196–3204. doi:10.1002/cber.19851180819.
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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[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.

Cyclopentadienone

Preparation

See also

References