Cyclopentadienone
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Preferred IUPAC name Cyclopenta-2,4-dien-1-one | |
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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]
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]
See also
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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CpH | He | ||||||||||||||||||||
LiCp | Be | B | CpMe | N | C5H4O | F | Ne | ||||||||||||||
NaCp | MgCp2 | Al | Si | P | S | Cl | Ar | ||||||||||||||
K | CaCp2 | ScCp3 | TiCp2Cl2 (TiCp2Cl)2 | VCp2 VCpCh | CrCp2 (CrCp(CO)3)2 | MnCp2 | FeCp2 Fe(η5-C5H4Li)2 | CoCp2 CoCp(CO)2 | NiCp2 | Cu | Zn | Ga | Ge | As | Se | Br | Kr | ||||
Rb | Sr | Y(C5H5)3 | ZrCp2Cl2 ZrCp2ClH | NbCp2Cl2 | MoCp2H2 MoCp2Cl2 | Tc | RuCp2 RuCp(PPh3)2Cl | RhCp2 | PdCp(C3H5) | Ag | Cd | InCp | SnCp2 | Sb | Te | I | Xe | ||||
Cs | Ba | * | LuCp3 | HfCp2Cl2 | Ta | (WCp(CO)3)2 | ReCp2H | OsCp2 | IrCp2 | Pt | Au | Hg | TlCp | PbCp2 | Bi | Po | At | Rn | |||
Fr | Ra | ** | Lr | Rf | Db | Sg | Bh | HsCp2 | Mt | Ds | Rg | Cn | Nh | Fl | Mc | Lv | Ts | Og | |||
* | LaCp3 | CeCp3 | PrCp3 | NdCp3 | PmCp3 | SmCp3 | Eu | Gd | Tb | DyCp3 | Ho | ErCp3 | TmCp3 | YbCp3 | |||||||
** | Ac | ThCp3 ThCp4 | Pa | UCp4 | Np | Pu | Am | Cm | Bk | Cf | Es | Fm | Md | No |
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