Excited state carbon acids: base catalysed photoketonization of dibenzosuberenol to dibenzosuberone via initial C–H bond heterolysis from S₁

Abstract

A new photoreaction, the photoketonization of dibenzosuberenol (1) to dibenzosuberone (2) in aqueous solution, is reported, the mechanism of which is believed to involve initial ionization of the C–H proton at the 5-position (in S1), to generate a 5-hydroxy-5-dibenzosuberenyl (9) carbanion intermediate.