Oxirene

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title: "Oxirene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["oxygen-heterocycles", "ethers", "three-membered-rings", "antiaromatic-compounds"] topic_path: "general/oxygen-heterocycles" source: "https://en.wikipedia.org/wiki/Oxirene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416814959 | ImageFileL1=oxiren.png | ImageSizeL1=80px | ImageFileR1=oxirene structure.png | ImageSizeR1=120px | ImageFile2=Oxirene-3D-vdW.png | ImageSize2=150px | PIN=Oxirene | SystematicName=Oxacyclopropene | OtherNames=Epoxyethene Ethyne oxide Acetylene oxide |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo=157-18-6 | PubChem=160438 | SMILES=C1=CO1 | ChemSpiderID_Ref = | ChemSpiderID = 140985 | InChI = 1/C2H2O/c1-2-3-1/h1-2H | InChIKey = BJEYNNFDAPPGST-UHFFFAOYAU | StdInChI_Ref = | StdInChI = 1S/C2H2O/c1-2-3-1/h1-2H | StdInChIKey_Ref = | StdInChIKey = BJEYNNFDAPPGST-UHFFFAOYSA-N | RTECS = | MeSHName = C012469 | ChEBI_Ref = | ChEBI = 30973 |Section2={{Chembox Properties | Formula=C2H2O | MolarMass=42.04 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = |Section8={{Chembox Related | OtherFunction = Ethylene oxide cyclopropane cyclopropene aziridine thiirane thiirene | OtherFunction_label = molecules with 3-membered rings | OtherCompounds =

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.

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.

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

References

References

  1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (March 2023). "Gas-phase detection of oxirene". Science Advances.
  3. (2003). "Assessment of density functional theory for the prediction of the nature of the oxirene stationary point". Journal of Molecular Structure: THEOCHEM.
  4. Lewars, Errol G.. (2011). "Computational Chemistry - Introduction to the Theory and Applications of Molecular and Quantum Mechanics". Springer.
  5. Kirmse, Wolfgang. (2002). "100 Years of the Wolff Rearrangement". European Journal of Organic Chemistry.
  6. (June 2001). "The Ozonolysis of AcetyleneA Quantum Chemical Investigation". Journal of the American Chemical Society.

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oxygen-heterocyclesethersthree-membered-ringsantiaromatic-compounds