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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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.
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.0K
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.
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Guidance on surface cyclization reactions through coordination structures.

Qing Wang1, Xiaoqing Liu1, Tianming Lu1

  • 1Department of Physics, Nanchang University, Nanchang 330031, People's Republic of China.

The Journal of Chemical Physics
|December 3, 2024
PubMed
Summary
This summary is machine-generated.

Metal coordination structures influence chemical reactions. On gold surfaces, 2,3-dibromo-6,7-dicyanonaphthalene (DDN) forms diverse products due to overlapping reaction temperatures, while on silver, it yields a single polymer via metal-induced cyclization.

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Area of Science:

  • Surface science
  • Organic chemistry
  • Materials science

Background:

  • Metal coordination structures are key to reaction pathways and products.
  • 2,3-dibromo-6,7-dicyanonaphthalene (DDN) possesses cyano and halogen functional groups.

Purpose of the Study:

  • Investigate the role of metal surfaces in regulating the reactivity of DDN.
  • Explore the formation of cyclization and polymerization products on different metal substrates.

Main Methods:

  • Scanning tunneling microscopy (STM) was used to study DDN on Au(111) and Ag(111) surfaces at room temperature.
  • Analysis of molecular self-assembly and reaction pathways on distinct metallic substrates.

Main Results:

  • On Au(111), overlapping reaction temperatures of bromine and cyano groups in DDN led to diverse C-C coupling and cyclization products.
  • On Ag(111), metal-coordinated structures directly induced a single type of polymer formation through cyclization.

Conclusions:

  • The interplay between metal coordination structures and the activation temperatures of functional groups dictates polymerization outcomes.
  • Surface-dependent reactivity of DDN highlights the importance of substrate interactions in controlling molecular transformations.