Study of supramolecular effect of tolanophanes in wacker-type oxidation

1,2-diketones are an important class of compounds which employed in synthesis of organic compoundssuch as imidazoles, quinoxalines, chiral 1,2diols. Several methods have been developed for synthesis of 1,2-diketones.wacker-type oxidation of alkynes catalyzed by PdBr2/CuBr2 was reported. The Pd-catalyzed Wacker oxidation is a well-known method for converting alkynes to carbonyl compounds [1]. Because of practical and environmental concerns, this transformation has recently received much attention. In continuous of our work on stilbenophanes [2-3], we now report our studyonoxidationtolanophanes1underwacker reaction.We first synthesized and characterized the diketones2. We also found thatthe Wacker oxidation of two defined tolanophaneswith different alkyl chain lengths gave the corresponding cyclic diketones in different rate. We concluded that the oxidation rate of tolanophanesshow the importance of supramolecular effect in elucidation of the reaction mechanism.