Reduction of 4,4′-Stilbenequinone and 4,4′-Diphenoquinone upon Reaction with Photogenerated Radicals

The properties of 3,3′,5,5′-tetra-tert-butyl-4,4′-stilbenequinone (StQ) were studied by photochemical means. Acetone, acetophenone or benzophenone was photolyzed in the presence of both StQ and a donor, such as alcohols or triethylamine. This initiated reaction of a ketyl radical with StQ to form a semiquinone radical and eventually induce a permanent bleaching due to conversion of StQ to 4,4′-dihydroxystilbene (StQH₂). The quantum yield of conversion of StQ to StQH₂ increases with the donor concentration. Similar effects were found for the ketone-sensitized radical-induced conversions of the analogous diphenoquinone to the reduction product, diphenol.