Chemistry:Cyclopropenone
From HandWiki
Cyclopropenone is an organic compound with molecular formula C
3H
2O consisting of a cyclopropene carbon framework with a ketone functional group. It is a colorless, volatile liquid that boils near room temperature.[1] Neat cyclopropenone polymerizes upon standing at room temperature,[2] and chemical vendors typically supply it as an acetal.[3] The chemical properties of the compound are dominated by the strong polarization of the carbonyl group, which gives a partial positive charge with aromatic stabilization on the ring and a partial negative charge on oxygen.[4][5] Cyclopropenone has been observed in the gas phase in interstellar environments such as the Taurus Molecular Cloud.[6]
See also
References
- ↑ R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041
- ↑ Breslow, Ronald; Oda, Masaji (1972-06-01). "Isolation and characterization of pure cyclopropenone". Journal of the American Chemical Society 94 (13): 4787–4788. doi:10.1021/ja00768a089. ISSN 0002-7863.
- ↑ Elliott, Gregory I.; Boger, Dale L.. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00486. "Dimethyl cyclopropenone ketal is less stable than the corresponding cyclic ketal derivatives....A direct route to cyclopropenone is the hydrolysis of 3,3‑dimethoxycyclopropene.".
- ↑ "Experiments show cyclopropenone is aromatic". Chem. Eng. News 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
- ↑ Peart, Patricia A.; Tovar, John D. (2010). "Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers". J. Org. Chem. 76 (15): 5689–5696. doi:10.1021/jo101108f. PMID 20704438.
- ↑ Hollis, J. M.; Remijan, Anthony J.; Jewell, P. R.; Lovas, F. J. (2006-05-10). "Cyclopropenone (c‐H 2 C 3 O): A New Interstellar Ring Molecule" (in en). The Astrophysical Journal 642 (2): 933–939. doi:10.1086/501121. ISSN 0004-637X. https://iopscience.iop.org/article/10.1086/501121.
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