Ring-Opening Functionalization of Simple gem-Difluorocyclopropanes by Single-Electron Oxidants

It was reported for the first time that single-electron oxidants such as CAN or K₂S₂O₈ affected facile ring opening of simple gem-difluorocyclopropanes to afford 1,3-dibromo-2,2-difluoropropanes in good yields by the action of KBr, and the appropriate choice of conditions allowed to incorporate not only second halogen atoms but also hydroxy or acetamido groups at the C¹ position in the difluoropropane structures in a regiospecific fashion after initiation of the reaction by the introduction of the first bromine atom at the C³ position.