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Related Concept Videos

Preparation of Epoxides03:00

Preparation of Epoxides

Overview
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 Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

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Related Experiment Video

Updated: May 12, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

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.

Liang Wang1, Wei Zhang2

  • 1School of Chemical and Pharmaceutical Engineering, Changzhou Vocational Institute of Engineering, Gehu Road 33, Wujin District, Changzhou, 213164, P. R. China.

Chemistry, an Asian Journal
|February 18, 2025
PubMed
Summary

Epoxides and aziridines are novel 1,3-dipole equivalents for synthesizing five-membered heterocycles via [3+2] annulation reactions. This review covers recent advances in epoxide- and aziridine-based annulations, focusing on diverse catalytic ring-opening conditions.

Keywords:
[3+2] annulationaziridineepoxideheterocyclesthree-membered ring

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

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Last Updated: May 12, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
10:14

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Heterocyclic Chemistry

Background:

  • [3+2] annulation reactions are key for synthesizing five-membered heterocyclic compounds.
  • Traditional methods often utilize O-centered and N-centered ylides.
  • Epoxides and aziridines offer alternative synthetic equivalents for 1,3-dipoles in these reactions.

Purpose of the Study:

  • To review recent advancements in [3+2] annulation reactions employing epoxides and aziridines.
  • To categorize these reactions based on their ring-opening mechanisms and catalytic conditions.
  • To highlight the utility of epoxides and aziridines in constructing functionalized heterocycles.

Main Methods:

  • Review of recent literature on epoxide- and aziridine-based [3+2] annulations.
  • Classification of reactions by ring-opening conditions: acid/base catalysis, organocatalysis, and transition-metal catalysis.
  • Analysis of reaction pathways, including concerted and formal cycloadditions.

Main Results:

  • Epoxides and aziridines effectively participate in [3+2] annulations with various dipolarophiles.
  • Diverse catalytic systems (acid/base, organocatalysis, transition-metal) enable controlled ring-opening and annulation.
  • These methods provide access to functionalized tetrahydrofurans, pyrrolidines, and related heterocyclic structures.

Conclusions:

  • Epoxide- and aziridine-based [3+2] annulations represent a versatile strategy for heterocyclic synthesis.
  • Catalysis plays a crucial role in controlling the reactivity and selectivity of these transformations.
  • These approaches expand the synthetic toolkit for accessing valuable five-membered heterocycles.