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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.
5.3K
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 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 Forming Bridged Bicyclic Products: Stereochemistry01:29

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6.5K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.1K

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Vibrational Spectra of a N719-Chromophore/Titania Interface from Empirical-Potential Molecular-Dynamics Simulation, Solvated by a Room Temperature Ionic Liquid
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Molecular Mode Selective Diels-Alder Cycloreversion under Vibrational Strong Coupling.

Gnana Maheswar Kothapalli1, Poulami Chakraborty1, Sourav Maiti1

  • 1Department of Chemical Sciences, Tata Institute of Fundamental Research, Mumbai, India, 400005.

The Journal of Physical Chemistry Letters
|April 2, 2026
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Summary
This summary is machine-generated.

Researchers achieved mode-selective control over chemical reactions using vibrational strong coupling (VSC). By tuning specific molecular vibrations, they influenced the Diels-Alder reaction kinetics, demonstrating a new light-matter interaction strategy.

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Area of Science:

  • Chemical Physics
  • Physical Chemistry
  • Spectroscopy

Background:

  • Vibrational strong coupling (VSC) offers novel ways to control chemical reactions.
  • Understanding how specific vibrational modes influence reaction dynamics is crucial.

Purpose of the Study:

  • To demonstrate mode-selective control of chemical reactivity using VSC.
  • To investigate the impact of coupling specific carbonyl vibrations in a cyclopentadienone dimer to a microcavity's optical mode on reaction kinetics.

Main Methods:

  • Utilized Diels-Alder cycloreversion of a cyclopentadienone dimer.
  • Employed Fabry-Pérot microcavity to achieve VSC.
  • Analyzed reaction kinetics and equilibrium shifts.
  • Performed frontier orbital analysis.

Main Results:

  • Selective coupling of the 1690 cm-1 allylic carbonyl stretch significantly modulated reactivity.
  • Coupling to a 1772 cm-1 localized carbonyl mode had minimal effect, showing mode selectivity.
  • Observed measurable shifts in monomer-dimer equilibrium and reaction kinetics.

Conclusions:

  • VSC enables precise control over chemical reactivity by targeting specific vibrational modes.
  • Orbital interactions, crucial for reactivity, can be tuned via targeted vibrational coupling.
  • This work presents a general strategy for controlling reaction pathways through light-matter interactions.