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

Literature Information

Publication Date 2007-01-15
DOI 10.1039/B616606G
Impact Factor 6.222
Authors

Matthias D'hooghe, Norbert De Kimpe


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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 of acetylene from an intermediate vinylamine as the key reaction steps.

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