N-Alkyl- and N-arylimines derived from o-allyl-, o-allyloxy-, and o-(2-propynyloxy)arenecarbaldehydes react with difluorocarbene to give indeno[1,2-b]pyrrole and chromeno[4,3-b]pyrrole derivatives. The reaction involves intermediate formation of difluoro-substituted azomethine ylides which undergo regio- and stereoselective intramolecular ring closure at the multiple bond.