SYNTHESIS OF NOVEL MONO-SUBSTITUTED AND DIARYL-SUBSTITUTED [2.2]PARACYCLOPHANES

The cross-coupling re actions of 4-bromo[2.2]paracyclophane with p-tol ylmagnesium bromide in the presence of various palladium and nickel co mplexes have been studied. It was found that [1,1'-bis(diphenylphosphi noferrocene)]palladium dichloride (PdCl2.dppf) shows the highest catal itic activity in this reaction. A series of new mono- and diaryl [2.2] paracyclophane derivatives with various substituents in the arene ring have been synthesized using this catalyst. It was shown that it is po ssible to cross-couple organozinc [2.2]paracyclophane derivatives with aromatic bromides. The composition and structure of the compounds obt ained have been established on the basis of elemental analysis and spe ctral data. Some correlations between the structure and spectral param eters of mono- and diaryl-substituted [2.2]paracyclophanes have been f ound.