Xie YS, Jiang H, Du CX, Zhu Y, Xu XL, Liu QL (2003) Structure and spectroscopic studies of 4,8-bis(2-Hydroxybenzyl)-cis-octahydro 1,4 -oxazino 3,2-b -1,4-oxazine. Structural Chemistry 14(3), 295-298. [In English]

Web link: http://dx.doi.org/10.1023/a:1023867914265

Keywords:

4,8-bis(2-hydroxybenzyl)-cis-octahydro[1,4]-oxazino [3,2-b]-1,4-oxazine; X-ray crystallography; IR spectroscopy; NMR spectroscopy; crystal-structure; complex;

Abstract: The title compound 4,8-bis(2-Hydroxybenzyl)-cis-octahydro [1,4]-oxazino [3,2-b]-1,4-oxazine ( 1) has been synthesized by the reaction of N-(2-hydroxybenzyl)-2-amino-1-ethanol with glyoxal. This novel compound was characterized by elemental analysis, IR, and H-1 NMR. The structure was also confirmed by a single crystal X-ray study. The compound crystallizes in monoclinic C2/C space group with unit cell dimensions: a = 18.318(4), b = 8.6110(17), c = 13.267(3) Angstrom, beta = 119.90(3)degrees, V = 1814.1(6) Angstrom(3), Z = 4. The two fused six-membered rings in 1 adopt chairlike conformations slightly flattened around the nitrogen atoms. In the central fusion bond, the geometry is a staggered conformation, with the two angular hydrogen atoms in the cis positions with respect to the rings, the nitrogen atoms antiperiplanar to each other, while the oxygen atoms remain gauche to each other and antiperiplanar to the hydrogen atoms. The ring conformations in 1 have been discussed on the basis of the anomeric effects and the presence of two strong intramolecular hydrogen bonds between the phenolic hydrogens and the amino groups.