Selective Cβ-O Bond Cleavage of Chalcone Epoxides Induced by Pyrylium Salt Sensitized Photoreactions and Dark Reactions with Cerium(IV) Salts

Article abstract of DOI:10.1016/S0040-4039(00)94495-2

The Cβ-O bonds of chalcone epoxides (1a, 1b) were selectively cleaved by pyrylium salt sensitized photoreactions, affording β-ketoaldehydes (2a, 2b) in CH2Cl2 and MeOH-adducts (3a, 3b) in MeOH.Similarly, cerium(IV) salts catalyzed the MeOH-adduct formations of 1a and 1b in the dark.On the other hand, nitrate ester (4b) was obtained on treatment of 1b with a cerium(IV) salt in MeCN.