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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
[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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Nitrogen heteroaromatic cations by [2+2+2] cycloaddition.

Martina Čížková1, Viliam Kolivoška, Ivana Císařová

  • 1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v. v. i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.

Organic & Biomolecular Chemistry
|November 5, 2010
PubMed
Summary

Researchers created versatile N-heteroaromatic frameworks using nitrogen quaternization and acetylene cycloaddition. A quinolinium system showed distinct redox states, enabling tunable electronic properties for advanced materials.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Quaternary N-heteroaromatic frameworks are crucial building blocks in various chemical applications.
  • Developing modular and flexible synthetic routes for these frameworks remains a significant challenge.

Purpose of the Study:

  • To establish a modular synthetic strategy for constructing diverse monocationic quaternary N-heteroaromatic frameworks.
  • To investigate the electrochemical properties of the synthesized quinolinium-based frameworks.

Main Methods:

  • Pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with acetylene.
  • Synthesis of 12 diverse scaffolds including pyridinium, quinolinium, thiazolium, benzothiazolium, imidazolium, and pyrimidinium derivatives.
  • Electrochemical analysis (cyclic voltammetry) to probe redox behavior.

Main Results:

  • Successful development of a modular synthetic route yielding 12 distinct N-heteroaromatic frameworks.
  • Demonstration of flexibility across multiple heterocyclic systems.
  • Identification of a quinolinium redox system with two electrochemically distinct forms (-0.7 V reduction, -0.05 V oxidation).
  • Observation of interconversion between redox states via homogeneous chemical reactions triggered by electron transfer.

Conclusions:

  • The developed modular approach offers a versatile platform for synthesizing a wide range of quaternary N-heteroaromatic compounds.
  • The electrochemical study highlights the potential of quinolinium frameworks in redox-active materials and electronic applications.