Solvent-controlled selective transformation of 2-bromomethyl-2-methylaziridines to functionalized aziridines and azetidines

The Journal of Organic Chemistry
Sonja StankovićNorbert De Kimpe

Abstract

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.

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Citations

May 23, 2017·Organic & Biomolecular Chemistry·Nicola PiensMatthias D'hooghe
Nov 3, 2016·Organic & Biomolecular Chemistry·Conor C G ScullyAndrei K Yudin
Jan 13, 2018·Organic & Biomolecular Chemistry·Esma B BoydasSaron Catak
Mar 20, 2014·Chemistry : a European Journal·Domingo Gomez Pardo, Janine Cossy
Apr 12, 2019·The Journal of Organic Chemistry·Maryne A J DuboisJames A Bull

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