How the combination of PhIO and I₂provides a species responsible for conducting organic reactions through radical mechanisms

Abstract

A combination of iodosobenzene (PhIO) and molecular iodine (I2) is well-documented to produce a key species capable of conducting various organic reactions through radical mechanisms. This key species is identified here by density functional theory (DFT) calculations to be the hypoiodite radical (IO). The calculations show that two equivalents of IO are generated when I2 reacts with two equivalents of PhIO. One of the ensuing IO species acts as a hydrogen abstractor and thus forms an organic radical and the other one is involved in oxidation of the resultant organic radical to afford the final product.