DIMERIZATION OF ANILINES AND BENZYLAMINES WITH MERCURY(II) OXIDE IODINE REAGENT

By treatment with mercury(II) oxide-iodine reagent in dichloromethane at room temperature, substituted anilines were transformed to the corr esponding azobenzenes. A similar treatment of benzylamines and benzhyd rylamine gave N-benzylidenebenzylamines and N-benzhydrylidenebenzhydry lamine, respectively. alpha-Alkyl-substituted benzylamines gave diazen es and the corresponding phenyl ketones, competitively. An azine was o btained by interaction with the reagent of a benzylamine carrying an e lectron-withdrawing substituent at the a position, such as ethyl pheny lglycinate. (C) 1998 Elsevier Science Ltd. AII rights reserved.