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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gollark: Dropping per-file headers entirely would make various things nicer, but also probably decrease the format's resilience to cryoapiaristic entities.

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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