Cyclopropenone

Cyclopropenone
	; Main resonance structures of cyclopropenone.
Names
	Preferred IUPAC name Cycloprop-2-en-1-one
	Other names Cyclopropenone, Cyclopropene-3-one
Identifiers
CAS Number	2961-80-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	121433;
PubChem CID	137779;
UNII	5MPZ6QZ6ZF ;
CompTox Dashboard (EPA)	DTXSID50183796 ;
	InChI InChI=1S/C3H2O/c4-3-1-2-3/h1-2H Key: GGRQLKPIJPFWEZ-UHFFFAOYSA-N; InChI=1/C3H2O/c4-3-1-2-3/h1-2H Key: GGRQLKPIJPFWEZ-UHFFFAOYAI;
	SMILES c1cc1=O;
Properties
Chemical formula	C3H2O
Molar mass	54.048 g·mol−1
Appearance	Colorless liquid
Melting point	−29 to −28 °C (−20 to −18 °F; 244 to 245 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopropenone is an organic compound with molecular formula C₃H₂O 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. It is an aromatic compound.^[4]^[5]

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. "Cyclopropene, 3,3‑Dimethoxy". 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.

[1] R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041

[2] 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.

[3] Elliott, Gregory I.; Boger, Dale L. "Cyclopropene, 3,3‑Dimethoxy". 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.

[4] "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.

[5] 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.

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See also

References