1366038-21-2Relevant academic research and scientific papers
Solvent-controlled selective transformation of 2-bromomethyl-2- methylaziridines to functionalized aziridines and azetidines
Stankovic, Sonja,Goossens, Hannelore,Catak, Saron,Tezcan, Meniz,Waroquier, Michel,Van Speybroeck, Veronique,D'Hooghe, Matthias,De Kimpe, Norbert
, p. 3181 - 3190 (2012)
The reactivity of 2-bromomethyl-2-methylaziridines toward oxygen, sulfur, and carbon nucleophiles in different solvent systems was investigated. Remarkably, the choice of the solvent has a profound influence on the reaction outcome, enabling the selective formation of either functionalized aziridines in dimethylformamide (through direct bromide displacement) or azetidines in acetonitrile (through rearrangement via a bicyclic aziridinium intermediate). In addition, the experimentally observed solvent-dependent behavior of 2-bromomethyl-2-methylaziridines was further supported by means of DFT calculations.
