124022-20-4Relevant academic research and scientific papers
Synthesis of the Bicyclo Ring Systems from 4-Allylcyclobutenones. Intramolecular Ketene/Alkene Cycloadditions
Xu, Simon L.,Xia, Haiji,Moore, Harold W.
, p. 6094 - 6103 (2007/10/02)
A general synthesis of bicycloheptenones from 4-allylcyclobutenones is described.The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2 + 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety.This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the substitution pattern is convenienty controlled.The scope of the rearrangement and the mechanism are discussed.
Rearrangements of Cyclobutenones. Conversion of Selected 4-Allylcyclobutenones to Bicycloheptenones
Xu, Simon L.,Moore, Harold W.
, p. 6018 - 6021 (2007/10/02)
4-Allyl-4-alkoxy(or hydroxy or (trimethylsilyl)oxy)cyclobutenones are reported to rearrange to bicyclohept-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 cycloaddition of the ketene moiety to the nonconjugated allylic double bond.
