Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes

The preparation of calixn]naphthalenes from derivatives of 2,7-dihydroxynaphthalene is described. 1,8-Dialkyl substitution is used to direct the regiochemistry of the acid-catalyzed condensation reactions. Acyclic peri substituents lead to a 3,5-linked calix3]naphthalene, whereas cyclic peri substituents give predominantly a calix5]naphthalene with the corresponding 3,6-linkage. The 3,6-linked calix4]naphthalene is prepared in pure form by a dimerization strategy.