Highly unusual conversion of 1-alkyl-2-(bromomethyl)aziridines into 1-alkyl-2-(N-alkyl-N-ethylaminomethyl)aziridines using methyllithium.
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 Et(2)O; 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 S(N)2'-type substitution at the aziridine moiety and liberation of acetylene from an intermediate vinylamine as the key reaction steps.
D'hooghe
Matthias
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium.
De Kimpe
Norbert
N
D001388:Aziridines / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009942:Organometallic Compounds / Q000737:chemistry*
D001388:Aziridines; D009942:Organometallic Compounds; C520093:methyllithium