Regiospecific fluorination of the aryl group in C6F5I and the preparation of C6F7IF2 - The first perfluorovinyl iodine(III) compound

Pentafluoroiodobenzene was oxidized regiospecificly by IF5/BF3 in CH2Cl2 to 1-iodo-heptafluoro-1,4-cyclohexadiene. With bromo- and chloro-pentafluorobenzene as substrates, the addition of two fluorine atoms to the aromatic ring proceeded analogously but more slowly. 1-Iodo-heptafluoro-1,4-cyclohexadiene was converted to 1-difluoroiodo-heptafluoro-1,4-cyclohexadiene by low-temperature fluorination. The thermal stability and reactivity of the first example of a perfluorinated vinyl iodine(III) compound are reported.