Design of new host compounds, cis-1,4-diphenylcyclohexane-1,4-diol, exo, exo-2,5-diphenylnorbornane-2,5-diol, exo-exo-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol and their derivatives

Abstract

The title host compounds were designed. Of these, cis-1,4-diphenylcyclohexane-1,4-diol (4) showed very high inclusion ability for alcohols and phenols, although its trans-isomer (3) showed none. By applying the selective inclusion complexation behaviour of 4, separation of isomers was accomplished. Rac-exo, exo-2,5-diphenylnorbornane-2,5-diol (9a) and rac-exo, exo-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol (11a) showed very poor inclusion ability. The optically active derivative of 11a (11b) showed none. In order to determine the reasons for the inclusion tendencies of the newly designed host compounds, molecular and crystal structures were studied by X-ray analysis.