Hypoiodite reaction: the mechanism of 1,2-diol fission

Abstract

The α-cleavage reaction of a vicinal diol with mercuric oxide–iodine reagent occurs in the dark at 0°, and the rate of fission is increased when the reaction mixture is irradiated. The fission reaction is thus suggested to occur by a heterolytic and/or homolytic process when the mixture is irradiated. cis- and trans-2,3-Bornane diols are split at the same rate; thus, the reagent is effective for the cleavage of trans-diols in non-polar solvents.