Isomeric oximes from 4,4,9,9-Tetramethyl-5,8-diazadodecane-2,11-dione

The preparation is reported of the ,&amino ketoxime 4,4,9,9-tetramethyl-5,8-diazadodecane-2,ll-dione dioxime. The synthesis yields a mixture of the syn (methyl) and anti isomers. The isomers are readily interconverted in solution in the presence of metal salts, acids, or alkali. Isomerically pure samples were isolated as di- and tetra-hydrochloride salts (syn isomer) and a dihydroperchlorate salt (anti isomer). The isomers have been characterized by the use of N.M.R. and infrared spectroscopy.