HYDROACRIDINES .16. STERIC EFFECT IN THE POLAROGRAPHIC-REDUCTION OF N-EPIMERIC AMINE OXIDES DERIVED FROM A-BETA,10A-ALPHA)-TETRADECAHYDRO-10-METHYLACRIDINE AND A-BETA,10A-ALPHA)-TETRADECAHYDRO-10-METHYLACRIDINE

The electrochemical reduction of (4a alpha,8a beta,9a beta,10 beta,10a alpha)-(1a), (4a alpha,8a beta,9a beta,10a,10a alpha)-(1e), (4a alpha ,8a alpha,9a beta,10 beta,10a alpha)-(2a) and (4a alpha,8a alpha,9a be ta,10 alpha,10a alpha)-tetradecahydro-10-methylacridine-10-oxide (2e) has been investigated by de and ac polarography. For both of these N-e pimeric pairs of amine oxides, the polarographic behaviour is influenc ed in the same way by the steric orientation of the N-O bond. So, wher eas the epimers with axial oxygen (1a and 2a) give normal, single-wave polarographic curves, both epimers with equatorial oxygen (1e and 2e) give unusually shaped, double-wave curves. The steric configuration o f the tricyclic framework affects only the values of the half-wave pot entials and not the shape of the polarographic curves. These results s uggest that polarography could be used to assign the steric configurat ions of the N-O bonds in saturated heterocyclic amine oxides, or to su pport assignments achieved by other methods.