Chemistry of. alpha.-halogenated imines. Part 31. Formation of. alpha.-cyanoaziridines and 1-(alkylamino) cyclopropanecarbonitriles by cyanation of. alpha.-halo …

N De Kimpe, P Sulmon, R Verhe…

Index: De Kimpe, Norbert; Sulmon, Paul; Verhe, Roland; De Buyck, Laurent; Schamp, Niceas Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4320 - 4326

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Citation Number: 30

Abstract

A new convenient synthesis of a-cyanoaziridines was developed by reaction of a-halo ketimines with cyanide in methanol or acetonitrile. Tertiary a-chloro ketimines with cyanide in methanol gave rise to a competitive reaction between a-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 ...