Formal Cycloaddition of Molecular Oxygen, 1,3-Diketone, and Olefin. Synthesis and Reactions of Cyclic Peroxides

Article abstract of DOI:10.1021/jo00275a025

Formal <2 + 2 + 2> cycloaddition of molecular oxygen, 1,3-diketones, and olefins took place by electrochemical oxidation.A catalytic amount of electricity was sufficient for the reaction, and an electroinitiated radical chain mechanism was proposed.The reaction was also initiated by a radical initiator.The resulting cyclic peroxides reacted with acids and some reducing agents such as ferrous sulfate, thiurea, and copper(I) chloride to give oxygen-oxygen bond cleavage products.