Related Experiment Video
Updated: May 12, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Recent Advances on Epoxide- and Aziridine-Based [3+2] Annulations
1School of Chemical and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, Gehu Road 33, Wujin District, Changzhou, 213164, P. R. China.
Abstract:
[3+2] Annulations are a powerful method for the synthesis of five-membered heterocyclic compounds. The annulations have concerted cycloaddition and formal (stepwise) cycloaddition reaction pathways. In addition to the well-established O-centered and N-centered ylides, epoxides and aziridines could serve as synthetic equivalent of 1,3-dipoles for [3+2] annulation with dipolarophiles for making functionalized tetrahydrofuran, pyrrolidine, and associated compounds. This review article covers recent development on epoxide- and aziridine-based [3+2] annulation reactions. The reactions are classified based on the ring opening conditions, including acid/base catalysis, organocatalysis, and transitional-metal catalysis.
Related Concept Videos
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Acid-Catalyzed Ring-Opening of Epoxides
Base-Catalyzed Ring-Opening of Epoxides
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

