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Updated: Nov 10, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthetic Applications of Aziridinium Ions
1Department of Chemistry, Hankuk University of Foreign Studies, Yongin 17035, Korea.
This review details the generation and synthetic applications of aziridinium ions, crucial intermediates for creating nitrogen-containing molecules. We explore their formation and selective reactions with nucleophiles for advanced organic synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Aziridines with electron-donating groups require activation to aziridinium ions for synthesis.
- Aziridinium ions are key intermediates in forming cyclic and acyclic nitrogen compounds.
Purpose of the Study:
- To review methods for generating aziridinium ions.
- To classify the formation of aziridinium ions (intra- and intermolecular).
- To describe the regio- and stereoselective transformations of aziridinium ions with nucleophiles.
Main Methods:
- Classification of intra- and intermolecular aziridinium ion formation.
- Analysis of recent developments in aziridinium ion chemistry.
- Description of nucleophilic addition reactions to aziridinium ions.
Main Results:
- Detailed classification of aziridinium ion generation pathways.
- Comprehensive overview of regio- and stereoselective nucleophilic additions.
- Highlighting recent advancements in the synthetic utility of aziridinium ions.
Conclusions:
- Aziridinium ion generation is essential for synthesizing diverse nitrogen-containing molecules.
- Understanding formation and reaction pathways enables precise synthetic control.
- Recent developments offer powerful tools for organic synthesis.
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