Synthesis of polymer intermediates containing the hexafluoroisopropylidene group via functionalization of 2,2-diphenylhexafluoropropane

The title compound was synthesized by hydrogenolysis of its precursor 2,2-bis(4-trifluoromethanesulfonatophenyl)hexafluoropropane ( 2 ) in the presence of a base. 2,2-Diphenylhexafluoropropane ( 6 ) can be appropriately functionalized at the 3,3′-positions to give the diamino ( 7 ), dibromo ( 11 ), dicarboxaldehydo ( 13 ), 3-ethynyl-3′-carboxaldehydo ( 14 ) derivatives which are important monomers in the synthesis of various high-temperatures resistant polymers and oligomers containing the hexafluoroisopropylidene (6F) group. 2,2-Bis(4-triflatophenyl)hexafluoropropane ( 2 ) undergoes quantitative dinitration at the 3,3′-positions to yield 2,2-bis(3-nitro-4-triflatophenyl)hexafluoropropane ( 3 ) which ultimately leads to the 3,3′-diamino-4,4′-bis(arylamino) ( 5 ) and 3,3′-diamino-4,4′-dihydroxy ( 8 ) derivatives which are specifically designed for phenylbenzimidazole, benzimidazoquinazoline, and benzoxazole polymers and oligomers.