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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

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

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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, the...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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

Diels–Alder Reaction: Characteristics of Dienophiles

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 on...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Synthetic protocol for diarylethenes through Suzuki-Miyaura coupling.

Satoru Hiroto1, Katsuya Suzuki, Hiroki Kamiya

  • 1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.

Chemical Communications (Cambridge, England)
|May 26, 2011
PubMed
Summary

Researchers synthesized diarylethenes using Suzuki-Miyaura coupling. This method efficiently incorporates thiophenes with cyano and ester groups into diarylethene structures.

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Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Diarylethenes are photochromic compounds with potential applications in molecular switches and optical memory devices.
  • Efficient synthesis methods are crucial for developing novel diarylethene derivatives.

Purpose of the Study:

  • To develop a versatile method for synthesizing diverse diarylethenes.
  • To incorporate functionalized thiophene units into diarylethene frameworks.

Main Methods:

  • Utilized the Suzuki-Miyaura coupling reaction.
  • Employed 1,2-dichlorohexafluorocyclopentene as a key building block.
  • Reacted with various arylboronic acids and esters.

Main Results:

  • Successfully synthesized a range of diarylethene compounds.
  • Demonstrated the incorporation of thiophenes bearing cyano and ester functionalities.
  • The Suzuki-Miyaura coupling proved effective for diarylethene synthesis.

Conclusions:

  • A robust synthetic route to functionalized diarylethenes has been established.
  • The developed method allows for the introduction of diverse substituents, expanding the scope of diarylethene chemistry.
  • This facilitates the design of diarylethenes for specific applications.