Abstract: 1-arylmethyl-2-(bromomethyl)aziridines were transformed into the corresponding 2-(cyanomethyl)aziridines and 2-(2-cyanoethyl)aziridines upon treatment with potassium cyanide in DMSO and a-lithiated trimethylsilylacetonitrile in THF, respectively. Further elaboration of 1-arylmethyl-2-(cyanomethyl)aziridines afforded 4-amino-2-butenenitriles, 3,4-diaminobutanenitriles and 2-aminocyclopropanecarbonitriles. Additionally, 1-arylmethyl-2-(2-cyanoethyl)aziridines were efficiently converted into biologically relevant 2-(aminomethyl)-cyclopropanecarbonitriles.