Generation of Radical Species from Cyclohexane-1,2-dione and the Reaction with Olefins: Preparation of 4,5-Dihydro-7(6H)-benzofuranone Derivatives

Article abstract of DOI:10.1246/bcsj.71.1437

Oxidation of cyclohexane-1,2-dione with ammonium hexanitratocerate(IV) (CAN) generates 2,3-dioxocyclohexyl radical, which reacts with electron-rich olefins to afford the corresponding addition products. The adducts thus generated are converted to 4,5-dihydro-7(6H)-benzofuranone by acid treatment. In addition to cyclohexane-1,2-dione, radical species are also generated from cyclopentane-1,2-dione and cycloheptane-1,2-dione.