| Revision as of 17:34, 2 May 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits {{heterocyclic-stub}}← Previous edit |
Latest revision as of 07:06, 8 December 2024 edit undoMrfoogles (talk | contribs)Extended confirmed users8,041 edits Add info, tag cite neededTag: Visual edit |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 396510228 |
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| verifiedrevid = 427098910 |
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| ImageFile = Oxetene.png |
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| ImageFile = Oxetene.svg |
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| ImageSize = 100px |
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| ImageSize = 100px |
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| IUPACName = 2''H''-Oxete |
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| PIN= 2''H''-Oxete |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = 1-Oxacyclobut-2-ene |
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| PubChem = 11970569 |
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|Section1={{Chembox Identifiers |
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| PubChem_Ref = {{pubchemcite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|pubchem}} |
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| ChemSpiderID = 10143952 |
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| CASNo = 287-25-2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI = 51195 |
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| PubChem = 11970569 |
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| ChemSpiderID = 10143952 |
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| SMILES = O1\C=C/C1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 51195 |
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| SMILES = O1\C=C/C1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H4O/c1-2-4-3-1/h1-2H,3H2 |
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| StdInChI = 1S/C3H4O/c1-2-4-3-1/h1-2H,3H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CRYATLIDHPPXDV-UHFFFAOYSA-N |
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| StdInChIKey = CRYATLIDHPPXDV-UHFFFAOYSA-N |
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| Beilstein = 4652799}} |
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| Beilstein = 4652799}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>3</sub>H<sub>4</sub>O |
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| Formula=C<sub>3</sub>H<sub>4</sub>O |
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| MolarMass=56.06326 |
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| MolarMass=56.06326 |
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|Section3={{Chembox Hazards |
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'''Oxetene''' is an unsaturated ]. The compound is unstable{{Citation needed|date=December 2024}} and has been synthesized.<ref>{{cite journal | title=Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete |author1=Friedrich, Louis |author2=Lam, Yuk-Sun | journal=The Journal of Organic Chemistry | year=1981 | volume=46 | issue=2 | pages=306–311 | doi=10.1021/jo00315a016}}</ref> Compared to ], the saturated compound, oxetene is destabilized because the double bond increases the ].{{Citation needed|date=December 2024}} Synthesis of some substituted derivatives has been reported.<ref name=":0">{{cite journal|doi=10.1081/SCC-120014973|title=A Convenient Synthesis of Oxetene Via Cycloaddition Reaction Under Microwave Irradiation|year=2002|last1=Longchar|first1=M.|last2=Bora|first2=U.|last3=Boruah|first3=R. C.|last4=Sandhu|first4=J. S.|journal=Synthetic Communications|volume=32|issue=23|pages=3611}}</ref><ref>{{cite journal|doi=10.1021/ja00536a069|title=Oxetene: Synthesis and energetics of electrocyclic ring opening|year=1980|last1=Martino|first1=Philip C.|last2=Shevlin|first2=Philip B.|journal=Journal of the American Chemical Society|volume=102|issue=16|pages=5429}}</ref> |
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Oxetene is less studied than ], a related compound that is the base of a number of organic molecules.<ref name=":0" /> |
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'''Oxetene''' is an insaturated ]. Unlike ], it is unstable and has not been synthesized<ref>Acheson, R. M. (1977), An Introduction to the Chemistry of Heterocyclic Compounds, John Wiley & Sons, p. 69, ISBN 0471002682</ref> because the double bond increases the ]. Synthesis of some substituted derivatives has been reported<ref>''Synthetic Communications'', 2002, 32:23, 3611-3616</ref><ref>''J. Am. Chem. Soc.'', 1980, 102(16), pp 5429–5430</ref>. |
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== Synthesis == |
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Oxetene can be synthesised by the photochemical cyclization of ]:<ref name="2H-Azirines">{{cite journal |author= Kikuchi O. |title = A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems |journal = Tetrahedron Lett.|volume= 22 |issue = 9 |pages= 859–862 |date = 1981 | doi =10.1016/0040-4039(81)80015-9}}</ref> |
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== References == |
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== References == |
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{{heterocyclic-stub}} |
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{{heterocyclic-stub}} |
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