Premium
Synthesis, structural and conformational study of 4‐α‐(or β)‐ p ‐chlorobenzoyloxy‐1‐azaadamantane hydrochloride
Author(s) -
Fernandez M. J.,
Galvez E.,
Lorente A.,
Soler J. A.,
Florencio F.,
Sanz J.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260215
Subject(s) - chemistry , cyclohexane , hydrochloride , epimer , piperidine , ring (chemistry) , stereochemistry , cyclohexane conformation , adamantane , nuclear magnetic resonance spectroscopy , crystallography , organic chemistry , molecule , hydrogen bond
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.