Novel Synthesis of N,N-Diarylarylmethanamines from N-(Arylmethylene)arenamines and (Arylmethoxy)arenes

Article abstract of DOI:10.1021/jo00020a032

Various N,N-diarylarylmethanamines were synthesized by the reaction of N-(arylmethylene)arenamines with (arylmethoxy)arenes in dimethylformamide solution in the presence of a strong base as a catalyst which is obtained in situ by reacting metallic sodium with this solvent.In general, the reaction may be depicted as the reduction of the imine and addition, on the original imino nitrogen atom, of the aryl group (of the aryloxy moiety) of the ether and presumably oxidation of the arylmethoxy group of the ether to its corresponding aldehyde.Side reactions and a proposed reaction mechanism are discussed.