Photochemical Formation of 1,5-Diketones from Dibenzoylmethane and Some Quinones

Irradiation (300 nm UV light) of dibenzoylmethane and 1,4-naphthoquinone in dichloromethane gave 1,5-dike-tone as the major product, along with β-hydroxyketone as the minor product. Anthraquinone and anthrone also added photochemically to dibenzoylmethane to give 1,5-diketones as the major products. In contrast, tetrahalo-1,4-benzoquinones added to dibenzoylmethane to give two types of 1,5-diketones via oxetane and cyclobutane intermediates. Comparison of the potential energy values of the photoproducts reveals that the 1,5-diketones are more stable than the corresponding oxetanes or cyclobutanes due to the ring-strain of the bicyclic compounds.