Hydroacridines. Part 17—Stereospecific influence of the N+—O- group on 1JC,C couplings in non-aromatic amine oxides
✍ Scribed by Francisc Potmischil; Helmut Herzog; Joachim Buddrus
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 213 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
The coupling constants of N-epimeric pairs of amine oxides derived from (4aa, 8ab, 9ab, 10aa)-1J C,C and (4aa, 8aa, 9ab, 10aa)-tetradecahydro-10-methylacridine, 1-cis-2,6-trimethylpiperidine and tropine were investigated and compared with those for the parent amines. For CÈC bonds adjacent to the NÈO~group, the couplings depend on the mutual orientation of the NÈO~bond and the CÈC bond of interest : with the NÈO~bond oriented syn (gauche), the couplings are essentially as large as those in the parent amines, whereas with the NÈO~bond oriented anti, the couplings are about 4È5 Hz smaller. The 13C NMR chemical shifts of the carbons, from which the conÐgurations of the N-epimeric amine oxides can be derived, are also reported.