Oxirene

Oxirene
Names
	Preferred IUPAC name Oxirene[1]
	Systematic IUPAC name Oxacyclopropene
	Other names Epoxyethene; Ethyne oxide; Acetylene oxide
Identifiers
CAS Number	157-18-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30973 ;
ChemSpider	140985 ;
MeSH	C012469
PubChem CID	160438;
CompTox Dashboard (EPA)	DTXSID20166177 ;
	InChI InChI=1S/C2H2O/c1-2-3-1/h1-2H Key: BJEYNNFDAPPGST-UHFFFAOYSA-N ; InChI=1/C2H2O/c1-2-3-1/h1-2H Key: BJEYNNFDAPPGST-UHFFFAOYAU;
	SMILES C1=CO1;
Properties
Chemical formula	C2H2O
Molar mass	42.04 g/mol
Related compounds
Related molecules with 3-membered rings	Ethylene oxide cyclopropane cyclopropene aziridine thiirane thiirene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Oxirene is a heterocyclic chemical compound which contains an unsaturated three-membered ring containing two carbon atoms and one oxygen atom. The molecule was synthesized in low temperature ices and detected upon sublimation by isomer selective photoionization reflectron time-of-flight mass spectrometry.[2]

Quantum chemical computational techniques found the configuration to be extremely strained and proposed an antiaromatic 4π electron system, as such oxirene is expected to be very high energy.[3][4]

Experimental indications exist that substituted oxirenes (as intermediates or transition states) may be involved in carbonylcarbene rearrangements observed in the Wolff rearrangement.[5] Computational evidence also point to the intermediacy of oxirenes in the ozonolysis of alkynes.[6]

References

"Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 146. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
Wang, Jia; Marks, Joshua; Turner, Andrew; Mebel, Alexander; Eckhardt, Andre; Kaiser, Ralf (March 2023). "Gas-phase detection of oxirene". Science Advances. 9 (10): eadg1134. Bibcode:2023SciA....9G1134W. doi:10.1126/sciadv.adg1134. PMC 10005165. PMID 36897943.
Mawhinney, Robert C; Goddard, John D (2003). "Assessment of density functional theory for the prediction of the nature of the oxirene stationary point". Journal of Molecular Structure: THEOCHEM. 629 (1–3): 263–270. doi:10.1016/S0166-1280(03)00198-2.
Lewars, Errol G. (2011). Computational Chemistry - Introduction to the Theory and Applications of Molecular and Quantum Mechanics (2nd ed.). Springer. doi:10.1007/978-90-481-3862-3. ISBN 978-90-481-3862-3.
Kirmse, Wolfgang (2002). "100 Years of the Wolff Rearrangement". European Journal of Organic Chemistry. 2002 (14): 2193–2256. doi:10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D.
Cremer, Dieter; Crehuet, Ramon; Anglada, Josep (June 2001). "The Ozonolysis of AcetyleneA Quantum Chemical Investigation". Journal of the American Chemical Society. 123 (25): 6127–6141. doi:10.1021/ja010166f. ISSN 0002-7863. PMID 11414847.

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[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 146. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] Wang, Jia; Marks, Joshua; Turner, Andrew; Mebel, Alexander; Eckhardt, Andre; Kaiser, Ralf (March 2023). "Gas-phase detection of oxirene". Science Advances. 9 (10): eadg1134. Bibcode:2023SciA....9G1134W. doi:10.1126/sciadv.adg1134. PMC 10005165. PMID 36897943.

[3] Mawhinney, Robert C; Goddard, John D (2003). "Assessment of density functional theory for the prediction of the nature of the oxirene stationary point". Journal of Molecular Structure: THEOCHEM. 629 (1–3): 263–270. doi:10.1016/S0166-1280(03)00198-2.

[4] Lewars, Errol G. (2011). Computational Chemistry - Introduction to the Theory and Applications of Molecular and Quantum Mechanics (2nd ed.). Springer. doi:10.1007/978-90-481-3862-3. ISBN 978-90-481-3862-3.

[5] Kirmse, Wolfgang (2002). "100 Years of the Wolff Rearrangement". European Journal of Organic Chemistry. 2002 (14): 2193–2256. doi:10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D.

[6] Cremer, Dieter; Crehuet, Ramon; Anglada, Josep (June 2001). "The Ozonolysis of AcetyleneA Quantum Chemical Investigation". Journal of the American Chemical Society. 123 (25): 6127–6141. doi:10.1021/ja010166f. ISSN 0002-7863. PMID 11414847.