Synthesis and Mutagenic Activity of Bay-Region Bridged Chrysenes

The synthesis of a series of substituted bay-region bridged chrysene derivatives is described. The method involves the oxidative photocyclization of stilbene carboxylic acids followed by dehydration with hydrofluoric acid. The photocyclization of stilbene carboxylic acids lead to secondary photolactonizations and functionalization of a bay region carbon by a novel photolytic process. The mutagenic activity of the substituted chrysenes was determined and activity levels correlated with substituent effects.