DIAZABICYCLOALKANES WITH NITROGEN ATOMS IN THE NODAL POSITIONS. 7. SYNTHESIS AND CONFIGURATION OF 2,3-DIPHENYL-1,4-DIAZABICYCLOOCTANE

Article abstract of DOI:10.1007/BF00513296

The reaction of ethylene oxide with the meso and d,l diastereomers of 1,2-diphenylethylenediamine gave N,N'-bis(β-hydroxyethyl)-1,2-diphenylethylenediamines, which upon refluxing with SOCl2 form N,N'-bis(β-chloroethyl)-1,2-ethylenediamines.The latter upon heating in dimethylformamide (DMF) at 150 deg C undergo cyclization to give, respectively, cis- and trans-2,3-diphenyl-1,4-diazabicyclo<2.2.2>octane.Evidence for the spatial orientation of the phenyl substituents in the diazabicyclooctanes obtained was obtained by means of an analysis of the multiplicity of the methylene protons in the PMR spectra.The vicinal spin-spin coupling constants for the benzyl protons of the isomeric 2,3-diphenyl-1,4-diazabicyclo<2.2.2>octanes in the 13C-H satellites were measured.The values obtained were compared with the literature data and with the dihedral angles calculated from mechanical models of the molecules.