Ketene imine ylides, generated from dichlorocarbene and diphenylketene alkyl- and arylimines undergo selective 1,3-dipolar cycloaddition to ethyl acrylate, methyl methacrylate, and acrylonitrile to give pyrrole and/or pyridine derivatives. The latter are formed by dichlorocyclopropanation of intermediate 2-chloropyrrolidones. A new type of transformation of ketene imine ylides to azomethine ylides was discovered in the reaction with methyl methacrylate.