Ring-opening reactions of methylenecyclopropanes with diphenyl diselenide upon heating; formation of 3-phenylselenyl-2,5-dihydrofuran derivatives

Abstract

The reactions of methylenecyclopropanes with diphenyl diselenide give ring-opened products in good yields at 150 [degree]C under nitrogen atmosphere for 3 h; the products can further undergo oxidative cyclization with hydrogen peroxide to furnish 3-phenylselenyl-2,5-dihydrofurans in moderate yields (three steps) at room temperature in CH(2)Cl(2) for 5 h; a plausible reaction mechanism has been proposed.