Chemical transformations of 2-phenylcyclopropane-1,1-dinitrile under the action of Lewis acids

The transformations of 2-phenylcyclopropane-1,1-dinitrile under the action of Lewis acids in the absence of interceptors of the resulting zwitterionic intermediates were explored. When such GaCl₃-based intermediate was decomposed with 10% HCl solution, (2-phenylethylidene)malonodinitrile was identified as the main product. The products of intramolecular annulation or dimerization, 1-amino-2-naphthonitrile or 3,5-diphenyl-2,3,5,6-tetrahydro-1H-pyrrolizine-1,1,7-tricarbonitrile, were also detected under certain reaction conditions.