3,5-Di-tert-butyl-o-benzoquinone as a reagent for oxidative dehydrogenation of 9R-symnonahydro-10-chalcogenoanthracenes

3,5-Di-tert-butyl-o-benzoquininone is a convenient reagent for the oxidative dehydrogenation of 9R-symnonahydro-10-chalcogenoanthracenes. The good solubility of o-quinone itself and the corresponding pyrocatechol facilitates the isolation of the salts of 10-chalcogenoanthrenes, which do not require additional purification. Unlike trityl perchlorate, o-quinone has mild oxidizing characteristics and does not give rise to elimination of the substituents. The synthesis of three new chalcogenopyrans and nine chalcogenopyrylium salts is described.