The first synthesis and characterization of both diastereomers of a di[2.2]paracyclophane:: 4,4′-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

The synthesis and characterization of both diastereomers, of a system comprised of two [2.2]paracyclophane units linked through a single 4,4' bond are described. Both the meso and d,l diastereomers of 4,4'-bis(octafluoro[2.2]paracyclophane) have been prepared via a palladium-catalyzed reductive homocoupling reaction by copper, producing a 3:2 ratio of meso and d,1 diastereomers. A similar reductive homocoupling of pseudo-o-iodotrifluoromethyloctafluoro[2.2]-paracyclophane gave only the analogous meso diastereomer. Single-crystal X-ray structures were obtained for all of the diparacyclophane products.