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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.
13.7K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.7K
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 more stable,...
5.7K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

5.3K
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.
5.3K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

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

6.8K
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.
6.8K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

8.5K
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...
8.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.6K

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The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
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Wolfium Bond Catalysis: Electronic Reprogramming and Transition State Stabilization in Aza-Diels-Alder Reactions.

Shaoli Liu1, Weichen Meng1, Heting Wang1

  • 1The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, P. R. China.

The Journal of Physical Chemistry. A
|April 2, 2026
PubMed
Summary

Wolfium bonds, a novel σ-hole interaction, effectively catalyze aza-Diels-Alder reactions by stabilizing imine reactants. This catalytic mechanism offers enhanced control over pericyclic reactions compared to traditional noncovalent bonds.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • Wolfium bonds, a type of σ-hole interaction involving Group 6 elements, have largely unexplored catalytic potential.
  • Understanding novel noncovalent interactions is crucial for developing new catalytic strategies in organic synthesis.

Purpose of the Study:

  • To systematically investigate the catalytic mechanism of wolfium bond donors (WnF4O, Wn = Cr, Mo, W) in the aza-Diels-Alder reaction.
  • To explore the role of wolfium bonds in modulating reaction pathways and activation barriers.
  • To compare the efficacy of wolfium bonds with conventional hydrogen and halogen bonds in catalysis.

Main Methods:

  • Theoretical investigation using density functional theory (DFT) calculations at the ωB97XD/aug-cc-pVTZ level.
  • Analysis of reaction mechanisms, activation barriers, and transition states.
  • Energy decomposition analysis (EDA) and Atoms in Molecules (AIM) analyses to characterize wolfium bond nature.
  • Solvent effect studies to evaluate catalyst performance in different media.

Main Results:

  • Wolfium bond donors catalyze the aza-Diels-Alder reaction via a prestabilization mechanism, significantly lowering activation barriers.
  • The catalytic efficiency follows the order Cr < Mo < W, attributed to increasing metal electronegativity and polarizability.
  • Wolfium bonds reprogram the reaction pathway to an asynchronous, charge-separated transition state, with electrostatic interactions dominating.
  • WF4O demonstrates effectiveness in both nonpolar and polar solvents, modulating the reaction pathway.

Conclusions:

  • Wolfium bonds represent a powerful new class of noncovalent interactions for catalyzing pericyclic reactions like the aza-Diels-Alder reaction.
  • These interactions offer superior control over reaction mechanisms compared to hydrogen and halogen bonds.
  • The findings provide a new perspective on the application of σ-hole interactions in catalysis and reaction design.