Site directed synthesis of mono and disubstituted SF5-polyfluoroalkyl benzenes

A novel method for the preparation of o-, m-, p-SF5CF2CFYC6H4X (Y = Br, F and X = m-Br, p-Br, Cl, CH3, CF3, NO2, o-NO2, F, CF3, CH(CH3)2) derivatives was devised by a two-step reaction: SF5Br-addition to o-, m-, p-CF2CFC6H4X followed by reaction of AgBF4 with the o-, m-, p-SF5CF2CFBrC6H4X adducts. Additional studies have been carried out with several derivatives and includes the preparation of SF5CF2C(O)C6H5, p-CF3CFBrC6H4NO2, SF5CF2CF2C6H3(NO2)2, SF5CF2CF2C6H3(NH2)2, and an SF5CF2CF2-containing polyimide and dye. The complete characterization (IR, NMR, and MS) of these compounds is given.