ANOMERIC CONFORMATIONS OF 6-MEMBERED CYCLIC AMINOXYL RADICALS WITH A BETA-ALKOXYL SUBSTITUENT

The addition reactions of CH3(CH2)(3)O-., (CH3)(2)CHCH2O., (CH3)(2)CHC H2CH2O., (CH3)(3)CO. and (CH3)(2)C(CN)O-. radicals to a novel six-memb ered cyclic nitrone, 6,6-dimethyl-3,4,5,6-tetrahydropyridine N-oxide ( M(2)PyO), generate the corresponding 6-alkoxyl-2,2-dimethylpiperidine- 1-oxyl aminoxyl (nitro ride) spin adducts, In benzene solution at room temperature, the preferential conformation of these spin adducts appe ars to be the anomeric conformer with the alkoxyl group in the axial p osition according to EPR spectroscopic conformational analysis of thes e aminoxyls. The anomeric effect in these aminoxyls might be the combi nation of electrostatic and molecular orbital interactions.