The Michael-induced ring closure (MIRC) of O-, S-, P- and C-nucleophiles with electrophilic allyl halides is a well established method for the synthesis of functionalized cyclopropanes. The far less investigated MIRC reaction of amines and imines with dialkyl 2-bromoalkylidenemalonates has been investigated and depending on the N-nucleophile used, a change in the reaction outcome was observed. With primary amines, dialkyl (2-iminoethyl)malonates were formed by ring opening of the intermediate unstable 2-aminocyclopropane-1,1-dicarboxylic esters. Secondary amines gave rise to the formation of dialkyl 2-aminoalkylidenemalonates, while diphenylmethylidenamine afforded the stable N-imino protected 2-(diphenylmethylidenamino)cyclopropane-1,1-dicarboxylic esters. The latter vicinally donor-acceptor substituted cyclopropanes proved sensitive to further ring opening and ring transformation reactions. γ-Diphenylmethylidenamino-γ-methoxy diesters were formed through methanolysis. Thermolysis in polar solvents afforded substituted 1-pyrrolines via a azavinylcyclopropane-azacyclopentene rearrangement. An efficient and synthetically useful ring transformation to 3-(alkoxycarbonyl)pyrrolidin-2-ones was accomplished by reduction of 2-(diphenylmethylidenamino)cyclopropane-1,1-dicarboxylic esters with sodium cyanoborohydride in the presence of acetic acid.