71201-44-0Relevant academic research and scientific papers
THE ELECTROCHEMICAL REDUCTION OF NN'-DISUBSTITUTED 6-PHENYL-2,3-DIHYDRO-1,4-DIAZEPINIUM SALTS: FORMATION OF BIS(TETRAHYDRODIAZEPINYLS) AND A DI-IMIDAZOLIDINYLBUTADIENE
Lloyd, Douglas,Vincent, Colin A.,Walton, David J.
, p. 801 - 805 (2007/10/02)
The NN'-disubstituted 6-phenyl-2,3-dihydro-1,4-diazepinium cations ( Ia-c ), in solution in dimethylformamide, undergo one electron single reduction waves at -0.9 to -1.3 V with respect to Ag-AgCl-KCl ( saturated ).The reductions were studied by polarography, cyclic voltammetry, and constant potential electrolysis.Rapid chemical reactions follow the initial reduction and isolated products were the bis(tetrahydrodiazepinyls) ( IV ) and ( VI ) and a di-imidazolidinylbutadiene ( V ).These producys were hydrolysed by concentrated hydrochloric acid to give the corresponding NN'-disubstituted ethylenediamine dihydrochloride and also, in the case of ( V ), 2,5-diphenylhexa-2,4-diene-1,6-dial.The meso-isomer ( IVa ) was converted into its racemic isomer ( IVb ) when heated in dimethylformamide.Compound ( IVb ) was quantitatively converted into the diene ( V ) in a cold mixture of chloroform and ethanol.Cyclic voltammetry studies of ( IV ) indicated that they were oxidised to bis(dihydrodiazepinium) cations, and that ( V ) was reduced, with similar behaviour to the reduction of 1,4-diphenylbuta-1,3-diene.
