Highly unusual conversion of 1-alkyl-2-(bromomethyl) aziridines into 1-alkyl-2-(N-alkyl-N-ethylaminomethyl) aziridines using methyllithium

M D'hooghe, N De Kimpe

Index: D'Hooghe, Matthias; Kimpe, Norbert De Chemical Communications, 2007 , # 12 p. 1275 - 1277

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Abstract

1-Alkyl-2-(bromomethyl) aziridines were transformed into 1-alkyl-2-(N-alkyl-N- ethylaminomethyl) aziridines upon treatment with 2–3 equiv. of methyllithium in THF or Et2O; the peculiarity in this transformation comprises the presence of an N-ethyl group in the end- products as well as the total number of carbon atoms, resulting from a highly unusual reaction course with a novel SN2′-type substitution at the aziridine moiety and liberation ...