Configurational and conformational study of new esters derived from 2-methyl-2-azabicyclo[2.2.2]octan-5-syn(anti)-ols by NMR spectroscopy and x-ray crystallography—I

✍ Scribed by M. J. Fernández; R. Huertas; M. S. Toledano; E. Gálvez; J. Server; M. Martínez-Ripoll

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 342 KB
• Volume: 35
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/(sici)1097-458x(199712)35:12<821::aid-omr181>3.0.co;2-7

✦ Synopsis

A series of esters derived from synand anti-2-methyl-2-azabicyclo [ 2.2.2 ] octan-5-ols were synthesized and studied by 1H, 13C and 2D NMR spectroscopy. The crystal structure of 5-syn-(3,5-dichlorobenzoyloxy)-2-methyl-2azabicyclo [ 2.2.2 ] octane was determined by x-ray di †raction. The unambiguous assignment of all bicyclic proton and carbon resonances was achieved by the combined analysis of the 1H-13C correlation spectra and double resonance experiments. The 1H-1H coupling constants are proposed as model values in order to carry out the analysis of other isoquinuclidine derivatives. In order to gain additional information, a conformational analysis using molecular modeling techniques was undertaken.