SYNTHESIS AND STRUCTURAL AND CONFORMATIONAL STUDY OF 3,7-DIMETHYL-3,7-DIAZABICYCLO[3.3.1]NONAN-9-ONE OXIME AND ITS TAUTOMER IMINE N-OXIDE

In an attempt to synthesize the 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one oxime hydrochloride, the corresponding tautomer imine N-oxide hydrochloride (I.HCl) was obtained, as deduced from X-ray and IR data. By neutralization of I.HCl, the corresponding oxime (II) was obtained and characterized by IR data. From the H-1 and C-13 NMR spectra of I.HCI and II, a twin-chair conformation for the bicyclic system, more flattened in II. was deduced. This conformation has also been shown by X-ray data for I.HCl.