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Communication | Regular issue | Vol 3, No. 2, 1975, pp.101-107
Published online, 1st January, 1970
DOI: 10.3987/R-1975-02-0101
The Preparation of Some CH2NMe3-Substituted Bicyclo[3.2.1]octanes. The Rotameric Behaviour of the CH2NMe3-Substituent

Robert Van Cauwenberghe, Marc Anteunis,* and Christian Becu

*Laboratory for NMR Spectroscopy, Department of Chemistry, State University of Gent, Krijgslaan 271 (S.4bis), B-9000 Gent, Belgium

Abstract

The conformations of cis-2-CH2X-4-Me-3,6,8-trioxa-bicyclo[3,2,1]octane (X=Cl, NMe3) and cis-2-CH2NMe3-4-Me-3,8-dioxa-6-aza-bicyclo[3,2,1]octane are investigated by 1H-NMR spectroscopy. As a result of the imposed conformation of the five membered ring-moiety, the orientation of the side-chain is that with the C2-N+ adjacent O3-C2 bonds in an antiperiplanar relationship. This situation corroborates a previously proposed parallelity effect between p-O and C-N+.