NMR study of 9-(1-adamantylaminomethyl)-9,10-dihydroanthracene and its β-cyclodextrin complexes

9-(1-Adamantylaminomethyl)-9,10-dihydroanthracene was prepared via condensation of adamantylnitrile with the 9-anthryllithium and its hydride reduction. An NMR study confirmed a boat conformation for the central ring, with the substituent of C-9 in a pseudo-axial position. The β-cyclodextrin host-guest complexes of the title compound and of the intermediate imine were studied from three points of view: the modification of chemical shift, the intermolecular NOE and the diffusion coefficients, all of which showed different behaviour. 1-Adamantylamine was used as a model to study the formation of the complex. Copyright © 2000 John Wiley & Sons, Ltd.