Dimerization of Anilines and Benzylamines with Mercury(II) Oxide-Iodine Reagent

Article abstract of DOI:10.1016/S0040-4020(98)00461-X

By treatment with mercury(II) oxide-iodine reagent in dichloromethane at room temperature, substituted anilines were transformed to the corresponding azobenzenes. A similar treatment of benzylamines and benzhydrylamine gave N-benzylidenebenzylamines and N-benzhydrylidene-benzhydrylamine, respectively. α-Alkyl-substituted benzylamines gave diazenes and the corresponding phenyl ketones, competitively. An azine was obtained by interaction with the reagent of a benzylamine carrying an electron-withdrawing substituent at the α position, such as ethyl phenylglycinate.