Oxetene Explained

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]

References

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