A photoenolization route to bicyclic ortho-quinodimethanes was investigated. Bicyclic photoenols were trapped in an intermolecular fashion with various dienophiles for the first time. All ortho-quinodimethane precursors were prepared via a selective route commencing with 1-indanol, α-tetralol and 1-benzosuberone. Irradiation afforded the E-photoenols exclusively which were trapped with equal efficiency except that derived from indane-4- ...
