ALL-HOMOCALIXARENES - CARBOCYCLIC HOST CO MPOUNDS WITH INTRAANNULAR AND EXTRAANNULAR LIGAND ARMS

Methoxy-substituted [2n]metacyclophanes 1-10, obtained by Muller-Rosch eisen cyclization, are converted into all-homocalixarenes 11-20 with f ree phenolic hydroxy functions. The well-soluble cyclic pentamer 11 an d octamer 14 with endo-acidic host properties are investigated with re gard to guest binding. They exhibit selectivity towards alkaline earth metal ions (Ba2+) in liquid/liquid extraction studies. Some of the ma crocyclic oligophenols are transformed into homocalixarenes 21-25 with intra- or extraannular oxapropionate groups. The diester 22 and the t etraester 23 are converted into carbocycles 26 and 27 with two and fou r free oxapropionic acid groups. Complexation properties of the oligoe sters in extraction studies and log K values in water are reported. X- ray structural analyses were performed of the [6]-, [8]- and [4]-homoc alixarenes 9 and 21, 14 and 23; the inclusion of solvent molecules is proven.