81401-24-3

Upstream product

• 98189-54-9 (2R,3S)-1-(2-Oxo-2-phenyl-ethyl)-2,3-diphenyl-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide 
• 98189-54-9 (2R,3R)-1-(2-Oxo-2-phenyl-ethyl)-2,3-diphenyl-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide 
• 81401-20-9 d,l-N,N'-bis(β-hydroxyethyl)-1,2-diphenyl-1,2-ethylenediamine 
• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 81401-22-1 d,l-N,N'-bis(β-chloroethyl)-1,2-diphenyl-1,2-ethylenediamine dihydrochloride 
• 81401-20-9 meso-N,N'-bis(β-hydroxyethyl)-1,2-diphenyl-1,2-ethylenediamine 
• 951-87-1 meso-1,2-diphenyl-1,2-diaminoethane 
• 81401-22-1 meso-N,N'-bis(β-chloroethyl)-1,2-diphenyl-1,2-ethylenediamine dihydrochloride 
• 106-93-4 ethylene dibromide 
• 70708-34-8 (±)-2,3-diphenylpiperazine 
• 104-71-2 N,N'-bis(benzyliden)ethylendiamine 
• 81601-99-2 (R,S)-2,3-diphenylpiperazine 
• 1609286-01-2 (R,S)-5,6-diphenylpiperazine-2,3-dione 

Downstream Products

• 81401-26-5 1-methyl-cis-2,3-diphenyl-1,4-azoniaazabicyclo<2.2.2>octane iodide 
• 81401-26-5 1-methyl-trans-2,3-diphenyl-1,4-azoniaazabicyclo<2.2.2>octane iodide 
• 98189-54-9 (2R,3R)-1-(2-Oxo-2-phenyl-ethyl)-2,3-diphenyl-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide 
• 98189-54-9 (2R,3S)-1-(2-Oxo-2-phenyl-ethyl)-2,3-diphenyl-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide 

Relevant academic research and scientific papers

Synthesis of chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octane derivatives

Racemic 2,3-diaryl-1,4-diazabicyclo[2.2.2]octane (DABCO) derivatives are synthesized from the readily accessible piperazines in 50-64% yield by cyclization using ethylene bromide, triethylamine, and KI at 80 °C. The enantiomerically enriched 2,3-diphenylpiperazine and the 2,3-bis(1-naphthyl)piperazine derivatives are prepared by a resolution method using commercially available optically active acids, yielding the corresponding DABCO derivatives in 51-64% yield with up to 99% ee. This mild cyclization can also be applied to enantiopure camphanyldiamine derivatives, and the products are obtained in 72-86% yields.

CHIRAL FLUORINATING REAGENTS

This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.

DIAZABICYCLOALKANES WITH NITROGEN ATOMS AT THE NODAL POSITIONS. 12. STEPHENS REARRANGEMENT IN SUBSTITUTED 1,4-DIAZABICYCLOOCTANES

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

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.