Oxirene

Oxirene

Names
IUPAC name Oxirene
Other names acetylene oxide, 1,2-epoxyethene, oxacyclopropene
Identifiers
CAS Number	157-18-6
3D model (Jmol)	Interactive image
ChEBI	CHEBI:30973
ChemSpider	140985
MeSH	C012469
PubChem	160438
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).
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Infobox references

Oxirene is a hypothesized heterocyclic chemical compound which contains an unsaturated three-membered ring containing two carbon atoms and one oxygen atom. As the configuration is extremely strained, no consensus exists whether the structure constitutes a molecule or whether it is merely a transition state.^[1] The substance is therefore mainly evaluated by molecular modeling techniques.

Experimental indications exist that oxirene (as intermediate or transition state) occurs in the Wolff rearrangement.

References

1. 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: 263. doi:10.1016/S0166-1280(03)00198-2.