
%0 Journal Article
%A Bayada, A 
%A Lawrance, GA 
%A Maeder, M 
%T Diammonium Salts Derived From 1,4-Diazabicyclo[2.2.2]octane
%J Australian Journal of Chemistry
%D 1994/01/01
%V 47
%N 1
%P 7-13
%K 
%R https://doi.org/10.1071/CH9940007
%U https://www.publish.csiro.au/paper/CH9940007 
%X The syntheses of a range of quaternary diammonium and some monoammonium salts derived from 1,4-diazabicyclo[2.2.2]octane with N-alkyl arms or N-alkyl arms terminated by a functional group are reported. In aqueous solution they are susceptible to only very slow Hofmann elimination, and the kinetics were investigated for the 1-(2&#8242;-ammonioethyl)-4-dodecyl-1,4-diazoniabicyclo[2.2.2]octane ion, which undergoes a base-induced elimination ( kOH 6.9&#215;10-4 dm3 mol-1 s-1 at 55&#176;C) consistent with an ElcB mechanism. In aqueous solution, the diammonium cations are not oxidized but undergo irreversible electrochemical reduction below -1.2 V v . Ag/ AgCl , with the reduction potential apparently influenced by the electron-withdrawing or -donating nature of substituent arms. 
