Coupling of 1-Alkyl-2-(bromomethyl)aziri­-dines with Lithium Dialkylcuprates towards 1,2-Dialkylaziridines

organometallics - nucleophilic substitution - 1,2-dialkyl­-aziridines

Significance

This work constitutes the first report of a reaction between an organocuprate and a 1-alkyl-2-(bromomethyl)aziridines 1. Thus 1 may be considered as a synthetic equivalent of an aziridinylmethyl cation 2. A variety of substituted 1,2-dialkylaziridines are be obtained by this route. However, in a few cases, using bis(isopropenyl)cuprate and lithium bis(allyl)cuprate, allyl­amines resulting from ring opening were isolated in 40-78%.

Comment

The reaction is of interest because, contrary to ring opening of a strained ring, either direct or via Payne rearrangement, side chain nucleophilic displacement is observed. 1,2-Dialkyl­aziridines are important substrates for making various cyclic and acyclic compounds such as oxazolidinones and 1,2-diamines.