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 compr ised 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 homo coupling reaction by copper, producing a 3:2 ratio of meso and d,1 diastere omers. A similar reductive homocoupling of pseudo-o-iodotrifluoromethylocta fluoro[2.2]-paracyclophane gave only the analogous meso diastereomer. Singl e-crystal X-ray structures were obtained for all of the diparacyclophane pr oducts.