Reaction of diimines and benzyne

The reaction between benzyne and the Schiff bases 1a,b and 15a,b leads to t he 1,4-bis(2'-substituted acridin-10-yl)benzene 4a,b, the N-phenylarylamine s 10a,b and the 10-(4'-formylphenyl)-substituted acridines iia,b (from la,b ) and the a-substituted acridine-10-carboxyaldehyde 18a,b (from 15a,b). Cyc lohexyl (4-cyclohexyliminomethylbenzylidine)amine 1c reacts with benzyne by an ene-reaction to give cyclohexenyl[(4-cyclchexyliminomethylphenyl)benzyl idine]amine 14. (C) 1999 Elsevier Science Ltd. All rights reserved.