Synthesis,structural and conformational study of 4-α-(or β)-p-chlorobenzoyloxy-1-azaadamantane hydrochloride

4-α-(or β)-p-Chlorobenzoyloxy-1-azaadamantane hydrochloride have been synthesized and studied by ¹H and ¹³C nmr spectroscopy, and the crystal structure of the α-epimer has been determined by X-ray diffraction. Each ring of the adamantane cage system is a nearly perfect chair, the substituted cyclohexane and piperidine rings, in endo and exo position respectively, having the biggest deviation. From the ¹H and ¹³C nmr data, several stereoelectronic effects have been deduced.