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Solvent-Controlled Selective Transformation of 2-Bromomethyl-2-methylaziridines to Functionalized Aziridines and Azetidines
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