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Related Concept Videos

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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
[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.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.

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Related Experiment Video

Updated: Jun 12, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Azide-Alkene Cycloaddition and Visible-Light-Mediated Wolff Rearrangement of Sugar Enones.

Oscar J Lamb1, Ben W Greatrex1

  • 1Faculty of Medicine and Health, University of New England, Armidale, NSW 2351, Australia.

The Journal of Organic Chemistry
|June 10, 2026
PubMed
Summary

Researchers synthesized branched carbohydrate β-amino esters from (-)-levoglucosenone (LGO) using a novel Wolff rearrangement. This method efficiently produces complex deoxyamino sugars with high stereocontrol.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

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Last Updated: Jun 12, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Synthetic Methodology

Background:

  • Carbohydrate derivatives are crucial in medicinal chemistry and biology.
  • Efficient synthesis of complex carbohydrate structures remains a challenge.

Purpose of the Study:

  • To develop a novel synthetic route to branched carbohydrate β-amino esters.
  • To utilize (-)-levoglucosenone (LGO) as a starting material for complex sugar synthesis.

Main Methods:

  • Azide-alkene cycloaddition on LGO catalyzed by methanesulfonic acid.
  • Visible-light-mediated Wolff rearrangement of diazoketones.
  • Optimization of solvent and temperature for improved ester yields.

Main Results:

  • Successful synthesis of branched deoxyamino sugars with high diastereoselectivity (>20:1).
  • Formation of ring-opened chiral 4-aminodihydrofurans via amine acylation/sulfonylation.
  • 2,2,2-Trifluoroethanol as an optimal solvent at subambient temperatures.

Conclusions:

  • The described Wolff rearrangement provides an efficient pathway to complex carbohydrate scaffolds.
  • The methodology offers a versatile approach for synthesizing functionalized amino sugars and dihydrofurans.