ISSN:
1434-4475
Keywords:
Keywords. Acridines, tetradecahydro; 13C NMR; 13C-Labelling; Stereoselective reactions.
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary. The stereoselectivities of the quaternization reactions of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine with methyl- and ethyl iodide as well as those of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-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 sterospecifically by equatorial approach, and the methylations of the N-ethyl amines occur by highly stereoselective (〉 90%) axial approach of the quaternizing reagent.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/PL00010310
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