The reaction of hexachloroacetone (HCA) with various diamines led eith
er to the corresponding diamides or to cyclic ureas, depending on the
molar ratio of the reactants. In the cases of ethylenediamine, 1,2-dia
minocyclohexane and o-phenylenediamine, the reaction with HCA also for
med bisimidazole derivatives. These latter unexpected products were al
so formed when the diamine reacted with trichloroacetate esters or wit
h carbon dioxide.