SYNTHESIS AND CONFORMATIONAL STUDIES OF PENTAHYDROXY[2.1.2.1.1]METACYCLOPHANES AND HEXAHYDROXY[2.1.1.1.1.1]METACYCLOPHANES

Base-catalyzed condensation of tyl-3-(5-tert-butylsalicyl)-2-hydroxyph enyl]ethane (8) with formaldehyde in xylene affords a novel ethylene-b ridged calixarene-analogous macrocyclic metacyclophane. However, not t he desired 2 has been obtained. Instead, the novel macrocyclic compoun ds pentahydroxy[2.1.2.1.1]- (9) and hexahydroxy-[2.1.1.1.1.1]metacyclo phane (10) have been isolated in 35 and 25% yields, respectively. The mechanism for the above disproportionation occurring during the base-c atalyzed condensation of 8 to afford these macrocyclic metacyclophanes and their H-1-NMR spectral behavior are discussed.