Synthesis, structural and conformational study of 4‐α‐(or β)‐<i>p</i>‐chlorobenzoyloxy‐1‐azaadamantane hydrochloride

Abstract

Abstract 4‐α‐(or β)‐ p ‐Chlorobenzoyloxy‐1‐azaadamantane hydrochloride have been synthesized and studied by 1 H and 13 C 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 1 H and 13 C nmr data, several stereoelectronic effects have been deduced.