Radical cyclization reaction of iodine containing fluoroolefines

Abstract We found that UV irradiation of 2-iodo-1,1,2,2-tetrafluoroethyl trifluorovinyl ether (3) or 3-iodo-1,1,2,2-tetrafluoropropyl trifluorovinyl ether (4) induces intermolecular atom transfer radical addition and produces a unique fluorine-containing oxetane and oxolane. The cyclized product acts as a radical precursor and adds to the olefin under UV irradiation. In addition, the difference in reactivity between 3 and 4 was clarified, and a double cyclization reaction of 4 with allylaniline was conducted.