Hydroacridines XXI [1]. ~13C NMR Spectroscopic Investigation of the Stereoselectivities of Quaternizations of N-Alkyl Derivatives of (4a#alpha#, 8a#beta#, 9a#beta#, 10a#alpha#)-and (4a#alpha#, 8a#alpha#, 9a#beta#, 10a#alpha#)-Tetradecahydroacridine

摘要

The stereoselectivities of the quaternization of (4a#apha#, 8a#beta#,9a#beta#,10a#alpha#)- and (4a#alpha#,8a#alpha#,9a#beta#,10a#alpha#)-tetradecahydro-10-methylacridine with methyl-and ethyl iodide as well as those of (4a#alpha#,8a#beta#,9a#beta#,10#alpha#0-and (4a#alpha#,8a#alpha#,9a#beta#,10a#alpha#)-10-ethyl-tetradecahydroacridine with methyl iodide were investigated using ~13C NMR spectroscopy including ~13C-labelling where appropriate. The methylations of both N-methyl amines occur by predominant (60% and 75%, respectively) equatorial approach, their ethylations occur stersopecifically by equatorial approach, and the methylations of the N-ethyl amines occur by highly stereoselective (>90%) axial approach of the quaternizing reagent.