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

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• 作者：Sonja Stankovi膰 ; Hannelore Goossens ; Saron Catak ; Meniz Tezcan ; Michel Waroquier ; Veronique Van Speybroeck ; Matthias D鈥檋ooghe ; Norbert De Kimpe
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：April 6, 2012
• 年：2012
• 卷：77
• 期：7
• 页码：3181-3190
• 全文大小：402K
• 年卷期：v.77,no.7(April 6, 2012)
• ISSN：1520-6904

文摘

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.