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[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

4.2K
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.
4.2K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.6K
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...
4.6K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.9K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.6K
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...
6.6K
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors01:31

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

5.3K
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.
5.3K

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An on-surface Diels-Alder reaction.

Jesús Castro-Esteban1, Florian Albrecht2, Shadi Fatayer2

  • 1Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782-, Santiago de Compostela, Spain.

Angewandte Chemie (International Ed. in English)
|October 19, 2021
PubMed
Summary

Researchers demonstrated a hexadehydro-Diels-Alder reaction on a surface using a single strained molecule. This advancement overcomes spatial limitations, enabling the iconic Diels-Alder reaction for on-surface synthesis and atom economy.

Keywords:
Diels-Alder reactionbond-resolved AFMcycloadditionon-surface synthesispolycyclic aromatic hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Surface Science
  • Nanotechnology

Background:

  • The Diels-Alder reaction is a cornerstone of organic synthesis but faces challenges in on-surface applications due to spatial constraints.
  • On-surface synthesis offers unique possibilities for constructing complex molecular architectures.
  • Developing new synthetic methodologies for surface-based reactions is crucial for molecular nanotechnology.

Purpose of the Study:

  • To demonstrate the feasibility of a hexadehydro-Diels-Alder reaction on a surface at the single-molecule level.
  • To overcome the spatial limitations typically associated with Diels-Alder reactions in on-surface synthesis.
  • To introduce the principle of atom economy into on-surface reaction design.

Main Methods:

  • Utilized a cyclic strained triyne as the reactant for the on-surface reaction.
  • Employed scanning probe microscopy, specifically atomic force microscopy (AFM) with CO-functionalized tips, for detailed reaction analysis.
  • Investigated the reaction mechanism and outcomes at the single-molecule level.

Main Results:

  • Successfully achieved an on-surface hexadehydro-Diels-Alder reaction within a single strained triyne molecule.
  • Atomic force microscopy provided detailed insights into the reaction process and product formation.
  • Demonstrated a novel application of a pericyclic reaction for on-surface molecular construction.

Conclusions:

  • The study successfully adapted the Diels-Alder reaction for on-surface synthesis, overcoming previous spatial limitations.
  • This work establishes a new pathway for utilizing complex pericyclic reactions in single-molecule surface chemistry.
  • The findings pave the way for employing atom-economical reactions in the burgeoning field of on-surface synthesis.