The reaction of para-substituted β-aminocinnamonitriles with benzonitrile oxides

β-Aminocinnamonitrile para-substituted by electron-withdrawing groups (5a,b) with benzonitrile oxides (2) give the expected cycloadducts (6) to the C–N triple bond. The p-methyl derivative (5c) behaves similarly, but the yields are smaller. Reactions of (2) with derivatives para-substituted by electron-donating groups (5d,e) give two bis-adducts, the structures of which have been elucidated.