Conformationally restricted calix[8]arenes substituted at all methylene bridges

Reaction under S(N)1 conditions of the octabromocalix8]arene derivative 2d with alcohols proceeds in nonstereoselective fashion, but all-cis octaryl derivatives are the single major products in the reaction with arenes. The incorporation of aryl substituents at the bridges rigidifies the calix8]arene skeleton.