Abstract
| - 1-Arylmethyl-2-(bromomethyl)aziridines were transformed into novel 2-(2-cyanoethyl)aziridines upontreatment with α-lithiated trimethylsilylacetonitrile in THF in an efficient and straightforward approach.The latter aziridines underwent ring opening by reaction with benzyl bromide in acetonitrile, affording5-amino-4-bromopentanenitriles through a regiospecific ring opening of intermediate aziridinium saltsby bromide. Further elaboration of these γ-bromonitriles resulted in the synthesis of novel 2-[N,N-bis(arylmethyl)aminomethyl]cyclopropanecarbonitriles in high yields by means of a 1,3-cyclization protocolupon treatment with KOtBu in THF.
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