RUTHENIUM-CATALYSED REARRANGEMENTS OF AZOBENZENES IV. REARRANGEMENTS OF DEUTERATED AZOBENZENES TO 1-PHENYLBENZIMIDAZOLE AND N-PHENYL-1,2-PHENYLENEDIAMINE DERIVATIVES

Article abstract of DOI:10.1016/0022-328X(85)80272-2

The ruthenium-catalysed reactions of azobenzene-d₁₀ and 4,4'-disubstituted azobenzene-d₈ compounds with non-deuterated tri-n-butylamine, n-butanol or 2-propanol give 1-phenylbenzimidazole or N-phenyl-1,2-phenylenediamine derivatives.The distibution of 1H in the aromatic rings of these products and in the recovered azobenzenes indicated that in all cases ortho-metallation of the azobenzene derivative has occured.The significance of those and other observations for the mechanism of these reactions is discussed.