Synthesis of 1-(2,4,6-Trifluorophenyl)perfluorobenzocyclobutene from Perfluorobenzocyclobutene and 1,3,5-Trifluorobenzene and Its Reaction with Polyfluorobenzenes in an SbF₅ Medium

The reaction of perfluorobenzocyclobutene with two equivalents of 1,3,5-trifluorobenzene in an SbF₅ medium followed by the treatment of the reaction mixture with water gave (3,4,5,6-tetrafluorobenzene-1,2-diyl)bis[(2,4,6-trifluorophenyl)methanone], 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobuten-1-ol, and 4,5,6,7-tetrafluoro-1,3,3-tris(2,4,6-trifluorophenyl)-1,3-dihydro-2-benzofuran-1-ol. The treatment of the reaction mixture with HF gave 1,2-bis(2,4,6-trifluorophenyl)-perfluorobenzocyclobutene and 1-(2,4,6-trifluorophenyl)perfluorobenzocyclobutene. The latter compound reacted with pentafluoro-, 1,2,3,4-, or 1,2,4,5-tetrafluorobenzenes in an SbF₅ medium to povide the corresponding perfluoro-1,2-diphenylbenzocyclobutenes after the treatment of the reaction mixture with HF.