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

Fernandez M. J. | Zendy; Galvez E. | Zendy; Lorente A. | Zendy; Soler J. A. | Zendy; Florencio F. | Zendy; Sanz J. | Zendy

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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.

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