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

Chem Commun (Camb). 2007 Mar 28:(12):1275-7. doi: 10.1039/b616606g. Epub 2007 Jan 15.

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 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.

MeSH terms

  • Aziridines / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Organometallic Compounds / chemistry*

Substances

  • Aziridines
  • Organometallic Compounds
  • methyllithium