Horning-crown macrocycles: novel hybrids of calixarenes and crown ethers

Org Lett. 2004 Sep 16;6(19):3261-4. doi: 10.1021/ol048921s.

Abstract

[reaction: see text] Novel macrocycles possessing ether linkages and 2,6-disubstituted phenolics were produced in one step and with 100% atom economy by isoaromatization of chameleon macrocyclic precursors possessing 2,6-diarylidenecyclohexanone moieties. Intramolecular hydrogen bonding of the phenolic hydrogen atoms influenced the shape of the macrocycles and dictated host-guest behavior.