Stereochemical studies—XXXVII: Saturated heterocycles—XIII Configuration and conformation of Z- and E-N-methyl- and -N- benzyl-2-p-nitrophenyl-4,5- and -5,6-tetramethylenetetrahydro-1,3-oxazines

The configuration and conformation of Z- and E-N-methyl- and -N-benzyl-2-p-nitrophenyl-4,5-, and -5,6-tetramethylenetetrahydro-1,3-oxazines were determined by ¹H and ¹³C NMR spectroscopy. The Z isomers were proved to be conformationally homogeneous, having the heteroatom in axial and equatorial position, respectively, in the case of the 5,6- and 4,5-tetramethylene compounds. Consequently, the p-nitrophenyl group and the anellated cyclohexyl ring are all-cis arranged in the Z-5,6-tetramethylene compounds while in the case of the Z-4,5-tetramethylene isomers the p-nitrophenyl group and the cyclohexyl ring are trans arranged to the hetero ring.