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- W2012140533 abstract "The synthesis and thermolysis of 4-allyl-4-arylcyclobutenones are detailed. Allylcyclobutenones were prepared through the trapping of the cyclobutenonium cation generated by treatment of 4-hydroxycyclobutenones with Lewis acids. A study of the nucleophilic trapping revealed the following mechanistic highlights: the most likely intermediate is the cyclobutenonium cation, the regioselectivity of the allylation reaction is dictated by attack at the site most suited to stabilize the cation, and the rate of allylation is dependent on carbocation formation. Thermolysis of 4-allyl-4-arylcyclobutenones made possible a study of the competitive [2 + 2] cycloaddition and 6π electrocyclization. A judicious choice of substituents allows some control of the selectivity between the two pathways. The substituents control this selectivity through a combination of imposed electronics in the dienylketene intermediate, the relative ketenophilicity of the 4-position substituent, and the relative contortion substituents in th..." @default.
- W2012140533 created "2016-06-24" @default.
- W2012140533 creator A5063378354 @default.
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- W2012140533 date "2010-06-13" @default.
- W2012140533 modified "2023-09-26" @default.
- W2012140533 title "ChemInform Abstract: Synthesis and Thermal Rearrangements of 4-Allyl-4-arylcyclobutenones." @default.
- W2012140533 cites W2949141557 @default.
- W2012140533 doi "https://doi.org/10.1002/chin.199942046" @default.
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