Photosolvolysis of 11H-benzo[b]fluoren-11-ol in aqueous solution

Abstract

The photosolvolysis of 11H-benzo[b]fluoren-11-ol (2), a 9-fluorenol derivative, has been studied in aqueous solution to test the hypothesis of enhanced photosolvolytic reactivity of these compounds. It is found that compared to the model compound, α-phenyl-2-naphthalenemethanol (3), 2 exhibited enhanced photosolvolytic reactivity. Quantum yields for photosolvolysis in aqueous alcohol solutions and steady-state and transient fluorescence studies are reported in neutral and acid solutions. The results further support the notion that an intrinsically accelerated photodehydroxylation step is associated with the formation of a 9-fluorenyl type carbocation intermediate (formally 4nπ electrons). Keywords: photosolvolysis, photodehydroxylation, carbocation.