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Related Concept Videos

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.7K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.0K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.0K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

4.8K
The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.
4.8K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.0K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.0K

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Water-Compatible Staudinger-Diels-Alder Ligation.

Masaru Tanioka1, Shohei Kanayama1, Fumino Kitamura1

  • 1Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.

The Journal of Organic Chemistry
|January 13, 2025
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Summary
This summary is machine-generated.

Staudinger-Diels-Alder (SDA) ligation shows promise as a new bioorthogonal reaction. Hydrophobic substituents on azide-benzocyclobutene (azide-BCB) improve its water tolerance for efficient C-C bond formation.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Reaction Engineering

Background:

  • Bioorthogonal reactions are crucial for advancing chemical biology.
  • Developing new reactions with enhanced stability and efficiency is an ongoing challenge.

Purpose of the Study:

  • To introduce and evaluate the Staudinger-Diels-Alder (SDA) ligation as a novel bioorthogonal reaction.
  • To investigate the impact of molecular structure on the reaction's performance in aqueous environments.

Main Methods:

  • Demonstration of Staudinger-Diels-Alder (SDA) ligation for forming C-C bonds at room temperature.
  • Systematic variation of aryl substituents on azide-benzocyclobutene (azide-BCB).
  • Mechanistic studies utilizing Density Functional Theory (DFT) calculations.

Main Results:

  • The SDA ligation successfully ligates two molecules via strong C-C bonds.
  • Aryl substituents on azide-BCB significantly influence water tolerance.
  • Chlorine-substituted azide-BCBs yielded high product formation even in water.
  • DFT analysis indicated hydrophobic electron-withdrawing groups suppress SDA ligation side reactions.

Conclusions:

  • Staudinger-Diels-Alder (SDA) ligation is a viable candidate for a new bioorthogonal reaction.
  • Optimizing substituents on azide-BCB is key to enhancing water tolerance.
  • The findings provide insights for designing robust bioorthogonal reactions for chemical biology applications.