Oxirene

Names

IUPAC name

Oxirene

Other names

acetylene oxide, 1,2-epoxyethene, oxacyclopropene

Identifiers

CAS Number

157-18-6^Y

3D model (Jmol)

CHEBI:30973^N

140985^N

InChI=1S/C2H2O/c1-2-3-1/h1-2H^N
Key: BJEYNNFDAPPGST-UHFFFAOYSA-N^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

↑ 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.

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