Journal of Organic Chemistry p. 6018 - 6021 (1989)
Update date:2022-09-26
Topics:
Xu, Simon L.
Moore, Harold W.
4-Allyl-4-alkoxy(or hydroxy or (trimethylsilyl)oxy)cyclobutenones are reported to rearrange to bicyclo<3.2.0>hept-2-en-7-ones upon thermolysis in refluxing toluene.The synthetic scope and mechanism of this unusual transformation are discussed.The products are envisaged to arise from an electrocyclic ring opening of the cyclobutenones to the corresponding vinylketenes which then undergo an intramolecular <2+2> cycloaddition of the ketene moiety to the nonconjugated allylic double bond.
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(1989)
