Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
J Org Chem. 2012 Apr 6;77(7):3181-90. doi: 10.1021/jo202637a. Epub 2012 Mar 15.
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.
研究了 2-溴甲基-2-甲基氮丙啶在不同溶剂体系中与氧、硫和碳亲核试剂的反应性。值得注意的是，溶剂的选择对反应结果有深远的影响，可以选择性地在二甲基甲酰胺中形成功能化的氮丙啶（通过直接溴取代）或在乙腈中形成氮杂环丁烷（通过双环氮丙啶中间体重排）。此外，通过 DFT 计算进一步证实了 2-溴甲基-2-甲基氮丙啶的实验观察到的溶剂依赖性行为。
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