HYDROACRIDINES PART-17 - STEREOSPECIFIC INFLUENCE OF THE N-O- GROUP ON (1)J(C,C) COUPLINGS IN NONAROMATIC AMINE OXIDES()

The (1)J(C,C) coupling constants of N-epimeric pairs of amine oxides d erived from (4a alpha, 8a beta, 9a beta, 10a alpha)- and (4a alpha, 8a alpha, 9a alpha, 10a alpha)-tetradecahydro-10-methylacridine, 1-cis-2 ,6-trimethylpiperidine and tropine were investigated and compared with those for the parent amines. For C-C bonds adjacent to the N+-O- grou p, the couplings depend on the mutual orientation of the N+-O- bond an d the C-C bond of interest: with the N+-O- bond oriented sm (gauche), the couplings are essentially as large as those in the parent amines, whereas with the N+-O- bond oriented anti, the couplings are about 4-5 Hz smaller. The C-13 NMR chemical shifts of the N-CH3 carbons, from w hich the configurations of the N-epimeric amine oxides can be derived, are also reported. (C) 1998 John Wiley & Sons, Ltd.