Reactions of mono- and bicyclic enol ethers with I₂–H₂O₂, I₂–Bu^tOOH, and I₂–tetrahydropyranyl hydroperoxide systems have been studied. It was shown that the reaction pathway depends on the nature of peroxide and the ring size. The reaction of 2,3-dihydrofuran and 3,4-dihydro-2H-pyran with the I₂–hydroperoxide system affords iodoperoxides, α-iodolactones, and α-iodohemiacetals. Bicyclic enol ethers are transformed into vicinal iodoperoxides only in the reaction with the I₂–H₂O₂ system, whereas the reaction with I₂–Bu^tOOH gives the hydroperoxidation product.