Hypoiodite reaction: mechanism of the reaction of mercury(II) oxide–iodine with olefins

Abstract

Evidence is presented that the reaction of mercury(II) oxide–iodine with olefins in aprotic solvents proceeds through ‘iodine oxide’. From a study of the products, which include rearranged carbonyl compounds, vinyl iodides, and 2,2′-di-iodo-ethers, and from an investigation of the reactions of epoxides and iodohydrins with morcury(II) oxide–iodine, it is concluded that ‘iodine oxide’ addition occurs by a regiospecific ionic mechanism initiated by attack on the double bond by positive iodine.