Synthesis and stereoisomerism of N-oxides of the decahydroquinoline series
The stereochemistry of the oxidation of epimeric (with respect to the 2 and 4 positions) 1-ethyl (n-propyl, n-butyl)-2-methyl-4-ethynyl-, 1,2,9-trimethyl-4-ethynyl(vinyl, ethyl, acetyl)-, and 1,2,2-trimethyl-4-ethynyl-trans-decahydro-4-quinolols was investigated. A preferred axial orientation of the N→O bond was established on the basis of a comparison of the chemical shifts of the 3-Haand 3-He protons of the bases and N-oxides.