Oxirene
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |||
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| Preferred IUPAC name
Oxirene[1] | |||
| Systematic IUPAC name
Oxacyclopropene | |||
| Other names
Epoxyethene Ethyne oxide Acetylene oxide | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChemSpider | |||
| MeSH | C012469 | ||
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| 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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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]