1366038-01-8Relevant academic research and scientific papers
LiAlH4-Induced Thia-Aza-Payne Rearrangement of Functionalized 2-(Thiocyanatomethyl)aziridines into 2-(Aminomethyl)thiiranes as an Entry to 5-(Chloromethyl)thiazolidin-2-ones
Dolfen, Jeroen,Van Hecke, Kristof,D'hooghe, Matthias
, p. 3229 - 3233 (2017/06/21)
Nonactivated 2-(thiocyanatomethyl)aziridines with diverse substitution patterns were deployed as substrates to effect a LiAlH4-promoted thia-aza-Payne rearrangement to provide access to functionalized 2-(aminomethyl)thiiranes in good to excelle
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
experimental part, p. 3181 - 3190 (2012/05/20)
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.
