Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers

Abstract

It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give previously unknown structures of 1-hydroperoxy-1′-alkoxyperoxides in yields up to 64%. The same compounds are formed in the iodine-catalyzed reactions of geminal bishydroperoxides with enol ethers. The nature of the solvent has a decisive influence on the formation of 1-hydroperoxy-1′-alkoxyperoxides. In the series of Et₂O, THF, EtOH, CHCl₃, CH₃CN, and hexane, the best results were obtained with the use of Et₂O or THF as the solvent.