Canadian Journal of Chemistry

The anomeric effect: The conformational equilibria of tetrahydro-1, 3-oxazines and 1-methyl-1, 3-diazane

H Booth, RU Lemieux

Index: Booth,H.; Lemieux,R.U. Canadian Journal of Chemistry, 1971 , vol. 49, p. 777 - 788

Full Text: HTML

Citation Number: 72

Abstract

By measurement of CH-NH coupling constants at low temperatures, the NH axial conformation was shown to be the dominant, or sole, conformation for tetrahydro-1, 3- oxazine, tetrahydro-2-methyl-1, 3-oxazine, and 1-methyl-1, 3-diazane. These results provide further experimental evidence for the generalized anomeric effect. Nuclear Overhauser experiments established the partial axial character of the N-methyl substituent in ...