A new convenient method is reported for the synthesis of the phenyl-capped
pentamer and hexamer of aniline. The method was accomplished by the reactio
n of the parent aniline tetramer in the pernigraniline oxidation state with
diphenylamine and N-phenyl-1,4-phenylenediamine in the leucoemeraldine oxi
dation state, respectively. The mechanism probably involves the formation o
f cation radicals and their coupling.