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Updated: May 12, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Electrochemical Ring Opening and [3 + 2] Cycloaddition of Aziridines: Access to 1,2-Bifunctionalized Products and
Shiv Dutt1, Neelam Duhan1, Vikas Kale1
1Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Punjab 140001, India.
Abstract:
Herein, we report an electricity-driven activation of aziridine via direct anodic oxidation to give N-heterocycles and 1,2-bifunctionalized products by excluding any oxidant/reductant or metal catalyst. Many structurally modified aziridines were employed in the presence of different nitriles. A large variety of nucleophiles were screened to furnish chemoselectively O-alkylated and C-alkylated products. Late-stage derivatization of aziridine with natural and medicinally active compounds has also been done. Remarkably, our strategy was found to be a greener, sustainable, and atom-economical approach (E-factor = ca. 0.8). Azetidine was also found to be compatible with our protocol and generated six-membered N-heterocycles. The detailed mechanistic study highlighted that the reaction is driven via the generation of an aziridine radical cation followed by the SN2 nucleophilic attack.
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