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A convenient and efficient procedure has been developed for the synthesis of 1-azidoadamantane, 1-adamantyl isocyanate, and 1-adamantyl isothiocyanate by reaction of 1,3-dehydroadamantane with hydrazoic, isocyanic, and isothiocyanic acids, respectively, under mild conditions. The reaction of 1,3-dehydroadamantane with hydrogen cyanide under analogous conditions gives adamantane-1-carbonitrile in a poor yield which may be improved using hexane as solvent.

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Abstract. This manuscript deals with the synthesis of various Adamantane derivatives as objects of supramolecular chemistry, in particular, supramolecular Cyclodextrine polymers (SCP) and Rotaxanes. One of the structural elements of the SCP and Rotaxanes are linear molecules modified by the end-blockers. A considerable volume of adamantyl group allows Adamantane derivatives to create locking groups in Rotaxanes, and a high affinity for β-Cyclodextrine to create supramolecular polymers.

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