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Synthesis and structural study of esters derived from 2‐methyl‐2‐azabicyclo[2.2.2]octan‐6‐ syn ( anti )‐ols by NMR spectroscopy and x‐ray crystallography
Author(s) -
Fernández M. J.,
Huertas R.,
Toledano M. S.,
Gálvez E.,
Cano F. H.,
Fonseca I.,
SanzAparicio J.
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199901)12:1<69::aid-poc92>3.0.co;2-0
Subject(s) - chemistry , octane , nuclear magnetic resonance spectroscopy , crystallography , bicyclic molecule , spectroscopy , crystal structure , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , x ray , organic chemistry , physics , quantum mechanics
A series of esters derived from syn ‐ and anti ‐2‐methyl‐2‐azabicyclo[2.2.2]octan‐6‐ols were synthesized and studied by NMR spectroscopy. The unambiguous assignment of all bicyclic proton and carbon resonances was achieved by the combined analysis of the COSY, 1 H– 13 C correlation spectra and double resonance experiments (spin decoupling). The crystal structure of 6‐ anti ‐(2‐chlorobenzoyloxy)‐2‐methyl‐2‐azabicyclo[2.2.2]octane hydrochloride, was determined by x‐ray diffraction, which confirmed the configurational assignment. Copyright © 1999 John Wiley & Sons, Ltd.