A convenient synthesis of new macrocyclic naphthalenophanes

Grützmacher H-F, Nolte G. A convenient synthesis of new macrocyclic naphthalenophanes. Chemische Berichte. 1994;127(6):1157-1162.The (1,4)naphthalenophanes 6a, 6b, 7a, and 7b were synthesized regiospecifically in two steps from the appropriate [alpha, beta]-di-1-naphthylalkanes by a Friedel-Crafts acetylation of the two naphthalene groups followed by cyclization/dimerization of the resulting diketones by a McMurray reaction. The macrocyclic naphthalenophanes 6a and 6b exist in solution as a mixture of conformers while 7a and 7b were identified as the anti isomers