[10]Paracyclophanediamides and their octadehydro derivatives: novel exotopic receptors with hydrogen-bonding sites on the bridge

2,9-Diaza-1,10-dioxo[10]paracyclophanes were prepared in short steps from the terephthaloyl chlorides via the corresponding 4,6-diyne derivatives, and the amide groups on the bridge endow the skeleton with the guest-binding properties as demonstrated by complexation with adrenaline by hydrogen bonds. The chiral auxiliaries on the bridge induce diastereomeric preference in terms of the planar chirality for the octadehydro derivative with a rigid diyne unit in crystal. (C) 2004 Elsevier Ltd. All rights reserved.