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Synthesis, structural and conformational study of 6‐hydroxy (or acyloxy) derivatives of the 1,3‐dimethyl‐1,3‐diazoniatricyclo[3.3.1.1 3–7 ]decane system
Author(s) -
Fernández M. J.,
Gálvez E.,
Lorente A.,
Camuñas J. A.,
Sanz J.,
Fonseca I.
Publication year - 1990
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.5570270533
Subject(s) - chemistry , decane , adamantane , ring (chemistry) , nuclear magnetic resonance spectroscopy , stereochemistry , crystal structure , crystallography , carbon 13 nmr , organic chemistry
1,3‐Dimethyl‐1,3‐diazoniatricyclo[3.3.1.1 3–7 ]decan‐6‐ol, and his p ‐chlorobenzoxy and diphenylacetoxy derivatives have been synthesized and studied by 1 H and 13 C nmr spectroscopy. The crystal structure of the alcohol 2a has been determined by X‐ray diffraction. Each ring of the adamantane cage system is a nearly perfect chair. From the 1 H and 13 C nmr data, several stereoelectronic effects have been deduced.