Fine regioselective tuning in the oxidation of sec,sec 1,2-diols by dimethyldioxirane

Article abstract of DOI:10.1016/0040-4020(96)00615-1

Non-symmetric sec,sec 1,2-diols and their o-isopropylidene derivatives undergo a regioselective oxidation by dimethyldioxirane depending on the electronic effects of the substituents. These results support previous views about the concerted O-insertion mechanism via a polar transition state.