Formation of α-Cyanoaziridines and 1-(Alkylamino)cyclopropanecarbonitriles by Cyanation of α-Halo Ketimines

Article abstract of DOI:10.1021/jo00171a033

A new convenient synthesis of α-cyanoaziridines was developed by reaction of α-halo ketimines with cyanide in methanol or acetonitrile.Tertiary α-chloro ketimines with cyanide in methanol gave rise to a competitive reaction between α-cyanoaziridine formation and production of 1-(alkylamino)cyclopropanecarbonitriles, the latter being classified as a Favorskii rearrangement-type product.The scope and limitations of this reaction have been determined by investigation of reaction parameters such as the nitrogen substituent, the solvent, the inorganic cyanide, the carbon skeleton, and the nature of the α-halogen.