Synthesis of bicyclo[2.2.2]octenones via modified Wessely oxidation of phenols

Abstract
The oxidation of ortho-substituted phenols with lead tetra-acetate in the presence of αβ-unsaturated acids followed by thermal intramolecular cycloaddition of the resulting cyclohexa-2,4-dienones provides a general method for the synthesis of bicyclo[2.2.2]octenones; such intramolecular reactions can lead to products that are regioisomers of related adducts formed by intermolecular Diels–Alder reactions.

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