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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
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.
5.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Updated: Apr 18, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Quinoxaline-Based Cyclo(oligophenylenes).

Lidia Marin1, Julija Kudrjasova, Pieter Verstappen

  • 1Design & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University , Agoralaan 1-Building D, 3590 Diepenbeek, Belgium.

The Journal of Organic Chemistry
|January 23, 2015
PubMed
Summary
This summary is machine-generated.

Fully conjugated quinoxaline macrocycles were synthesized using Ni(0)-mediated coupling. The resulting cyclotrimers and cyclotetramers show potential for host-guest chemistry and organic electronics applications.

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Quinoxaline derivatives are important building blocks in organic electronics.
  • Macrocyclic compounds offer unique structural and electronic properties.
  • Developing efficient synthetic routes for conjugated macrocycles is crucial.

Purpose of the Study:

  • To synthesize novel fully conjugated quinoxaline-based oligophenylene macrocycles.
  • To investigate the structural and optoelectronic properties of these macrocycles.
  • To explore their potential applications in host-guest chemistry and organic electronics.

Main Methods:

  • Ni(0)-mediated Yamamoto-type diaryl homocoupling reaction.
  • Synthesis of (fluorinated) 2,3-bis(4'-bromophenyl)quinoxaline precursors.
  • Characterization using single-crystal X-ray diffraction and spectroscopic techniques.

Main Results:

  • Successful synthesis of quinoxaline-based cyclotrimers and cyclotetramers as dominant products.
  • Full structural characterization, including X-ray crystal structures.
  • Analysis of optoelectronic properties revealing potential for electronic applications.

Conclusions:

  • The study demonstrates a viable method for synthesizing conjugated quinoxaline macrocycles.
  • The characterized macrocycles possess properties suitable for host-guest chemistry.
  • These novel materials hold promise for advancements in organic electronics.