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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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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: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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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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Noncovalent Dimerization after Enediyne Cyclization on Au(111).

Dimas G de Oteyza1,2, Alejandro Pérez Paz3, Yen-Chia Chen4

  • 1Donostia International Physics Center , E-20018 San Sebastián, Spain.

Journal of the American Chemical Society
|August 5, 2016
PubMed
Summary
This summary is machine-generated.

On gold surfaces, 1,2-bis(2-phenylethynyl)benzene undergoes thermal cyclization preferentially via the C(1)-C(6) pathway, forming a strained bicyclic olefin. This product then self-assembles into noncovalent dimers.

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Area of Science:

  • Surface chemistry
  • Organic synthesis
  • Computational chemistry

Background:

  • Enediyne cyclization in solution involves competing C(1)-C(6) (Bergman) and C(1)-C(5) pathways.
  • The surface chemistry of sterically hindered enediyne cyclization products is largely unexplored.

Purpose of the Study:

  • To investigate the thermally induced cyclization of 1,2-bis(2-phenylethynyl)benzene on a gold surface.
  • To elucidate the reaction mechanism and product self-assembly behavior.
  • To understand the influence of the Au(111) surface on the cyclization pathway.

Main Methods:

  • Scanning tunneling microscopy (STM) for surface observation.
  • Computer simulations for theoretical analysis.
  • Density functional theory (DFT) calculations for mechanism and driving forces.

Main Results:

  • The C(1)-C(5) cyclization pathway is suppressed on Au(111).
  • The C(1)-C(6) cyclization yields a novel, highly strained bicyclic olefin.
  • The bicyclic olefin product self-assembles into discrete, noncovalently bound dimers on the Au(111) surface.

Conclusions:

  • The Au(111) surface directs the cyclization of 1,2-bis(2-phenylethynyl)benzene towards the C(1)-C(6) pathway.
  • A unique strained bicyclic olefin is formed and exhibits self-assembly into dimers.
  • DFT calculations provide insights into the reaction mechanism and noncovalent interactions driving dimer formation.