Dehydrogenation of 7,12-Dihydropleiadene Compounds with High Potential Quinones

Dehydrogenation with high potential quinones has been extended to dihydro derivatives of non-aromatic hydrocarbons using 7,12-dihydropleiadenes as models. Reaction of 7-phenyl-7,12-dihydropleiadene with high potential quinones resulted in dehydrogenative cyclization whereas preparative scale and rate studies in 9-aryl-9,10-dihydroanthracenes gave no evidence of aryl participation during quinone dehydrogenation due to geometrical restrictions on this system.