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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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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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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Cycloaddition Reactions: Overview01:16

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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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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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.
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Site-Specific Surface Modification via Chemoselective Click Reactions on Cyclobutene-Functionalized Monolayers.

Boone W Evans1, Kenneth N Hipp1, William D Lambert1

  • 1Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska, USA.

Chemistryopen
|March 30, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces self-assembled monolayers with cyclobutene for surface modification. These monolayers enable efficient chemical reactions, allowing for controlled bisfunctionalization via Diels-Alder and click chemistry.

Keywords:
clickcyclobuteneelectrochemical sensinginverse electron‐demand Diels–Alderself‐assembled monolayers

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Area of Science:

  • Surface chemistry
  • Organic chemistry
  • Materials science

Background:

  • Self-assembled monolayers (SAMs) are crucial for surface functionalization.
  • Cyclobutene moieties offer unique reactivity for chemical modifications.
  • Gold surfaces are widely used platforms for SAMs.

Purpose of the Study:

  • To report the first SAMs incorporating cyclobutene-substituted alkanethiols on gold.
  • To demonstrate efficient monolayer modification using inverse electron-demand Diels-Alder (IEDDA) cycloadditions.
  • To achieve controlled bisfunctionalization of mixed SAMs.

Main Methods:

  • Formation of SAMs on gold surfaces using cyclobutene- and azide-substituted alkanethiols.
  • Application of inverse electron-demand Diels-Alder (IEDDA) cycloadditions for surface modification.
  • Utilizing copper-assisted alkyne/azide cycloaddition (CuAAC) ligation for bisfunctionalization.

Main Results:

  • Successful incorporation of cyclobutene-substituted alkanethiols into SAMs on gold.
  • Efficient modification of these SAMs via IEDDA cycloadditions.
  • Demonstrated controlled bisfunctionalization of mixed SAMs using sequential or simultaneous IEDDA and CuAAC reactions.

Conclusions:

  • This work presents a novel approach for creating functionalized surfaces using cyclobutene-containing SAMs.
  • The developed method allows for precise control over surface modification through orthogonal click chemistry reactions.
  • These findings open new avenues for advanced materials and surface engineering.