81401-26-5Relevant academic research and scientific papers
DIAZABICYCLOALKANES WITH NITROGEN ATOMS AT THE NODAL POSITIONS. 12. STEPHENS REARRANGEMENT IN SUBSTITUTED 1,4-DIAZABICYCLOOCTANES
Vysochin, V. I.,Shishkin, G. V.
, p. 559 - 563 (2007/10/02)
The ylides formed from phenacyl derivatives of substituted diazabicyclooctanes decompose to the initial base or give products of the Stephens rearrangement, leading to an expansion of the ring.The direction of the reaction is determined by the presence of
DIAZABICYCLOALKANES WITH NITROGEN ATOMS IN THE NODAL POSITIONS. 7. SYNTHESIS AND CONFIGURATION OF 2,3-DIPHENYL-1,4-DIAZABICYCLOOCTANE
Shishkin, G. V.,Naumenko, I. I.,Anisimova, I. L.,Yudina, O. B.,Storozhenko, V. G.
, p. 80 - 84 (2007/10/02)
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-diazabicyclooctane.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-diazabicyclooctanes 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.
