Abstract
The reaction of ethylene oxide with the meso and d,l diasteromers of 1,2-diphenyl-ethylenediamine 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 ° C undergo cyclization to give, respectivley, 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.
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See [1] for Communication 6.
Translated from Khimiya Geterotsiklicheskikh Soedinenii. No. 1. pp. 95–100. January, 1982.
The authors thank V. I. Mamatyuk and Yu. V. Gatilov for their assistance in interpreting the PMR spectra and performing the mathematical calculations.
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Shishkin, G.V., Naumenko, I.I., Anisimova, I.L. et al. Diazabicycloalkanes with nitrogen atoms in the nodal positions. 7. Synthesis and configuration of 2,3-diphenyl-1,4-diazabicyclo[2.2.2]-octane. Chem Heterocycl Compd 18, 80–84 (1982). https://doi.org/10.1007/BF00513296
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DOI: https://doi.org/10.1007/BF00513296