Oxetene

Oxetene
Names
	Preferred IUPAC name 2H-Oxete
	Systematic IUPAC name 1-Oxacyclobut-2-ene
Identifiers
CAS Number	287-25-2 [pubchem];
3D model (JSmol)	Interactive image;
Beilstein Reference	4652799
ChEBI	CHEBI:51195 ;
ChemSpider	10143952 ;
PubChem CID	11970569;
CompTox Dashboard (EPA)	DTXSID20474941 ;
	InChI InChI=1S/C3H4O/c1-2-4-3-1/h1-2H,3H2 Key: CRYATLIDHPPXDV-UHFFFAOYSA-N ;
	SMILES O1\C=C/C1;
Properties
Chemical formula	C3H4O
Molar mass	56.06326
	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

Oxetene is an unsaturated heterocycle. The compound is unstable and has been synthesized.[1] Compared to oxetane, the saturated compound, oxetene is destabilized because the double bond increases the ring strain. Synthesis of some substituted derivatives has been reported.[2][3]

Synthesis

Oxetene can be synthesised by the photochemical cyclization of acrolein:[4]

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References

Friedrich, Louis; Lam, Yuk-Sun (1981). "Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete". The Journal of Organic Chemistry. 46 (2): 306–311. doi:10.1021/jo00315a016.
Longchar, M.; Bora, U.; Boruah, R. C.; Sandhu, J. S. (2002). "A Convenient Synthesis of Oxetene Via [2+2]Cycloaddition Reaction Under Microwave Irradiation". Synthetic Communications. 32 (23): 3611. doi:10.1081/SCC-120014973.
Martino, Philip C.; Shevlin, Philip B. (1980). "Oxetene: Synthesis and energetics of electrocyclic ring opening". Journal of the American Chemical Society. 102 (16): 5429. doi:10.1021/ja00536a069.
Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862. doi:10.1016/0040-4039(81)80015-9.

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[1] Friedrich, Louis; Lam, Yuk-Sun (1981). "Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete". The Journal of Organic Chemistry. 46 (2): 306–311. doi:10.1021/jo00315a016.

[2] Longchar, M.; Bora, U.; Boruah, R. C.; Sandhu, J. S. (2002). "A Convenient Synthesis of Oxetene Via [2+2]Cycloaddition Reaction Under Microwave Irradiation". Synthetic Communications. 32 (23): 3611. doi:10.1081/SCC-120014973.

[3] Martino, Philip C.; Shevlin, Philip B. (1980). "Oxetene: Synthesis and energetics of electrocyclic ring opening". Journal of the American Chemical Society. 102 (16): 5429. doi:10.1021/ja00536a069.

[2H-Azirines-4] Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862. doi:10.1016/0040-4039(81)80015-9.