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Photoacylation of Electron-Rich Quinones: An Application of the ”Photo-Friedel-Crafts Reaction”
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2002
Year
Chemical EngineeringDerivative (Chemistry)EngineeringPhotoredox ProcessPhotochemistry5-Acetyloxy Naphthoquinone 8Mechanistic PhotochemistryPhotocatalysisOrganic ChemistryAcylated HydroquinonesChemistryHeterocycle ChemistryPharmacologyElectron-rich QuinonesSynthetic ChemistryGood Yields
Irradiation of substituted 1,4-benzo- or 1,4-naphthoquinones in the presence of several aldehydes resulted in the formation of acylated hydroquinones in good yields. In the case of 5-acetyloxy naphthoquinone 8, both regioisomers were formed, but the 2,8-isomer was favored in all cases examined. Even acylated tetrahydroxy naphthalenes became available in good yields by this method.