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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
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

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
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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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Can Twisted Double Bonds Facilitate Stepwise [2 + 2] Cycloadditions?

Renan V Viesser1, Clayton P Donald1, Jeremy A May1

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204, United States.

Organic Letters
|April 29, 2024
PubMed
Summary
This summary is machine-generated.

Highly twisted anti-Bredt alkenes with small singlet-triplet energy gaps may undergo facile [2 + 2] cycloadditions. Computational studies explored ethylene, acetylene, perfluoroethylene, and cyclooctyne reactions.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • Anti-Bredt alkenes feature strained bridgehead double bonds.
  • Understanding their reactivity is crucial for synthetic chemistry.

Purpose of the Study:

  • Investigate the potential for [2 + 2] cycloaddition reactions in anti-Bredt alkenes.
  • Identify structural features that promote facile cycloaddition.

Main Methods:

  • Utilized computational studies to analyze reaction pathways.
  • Examined a series of anti-Bredt alkenes with varying degrees of strain.

Main Results:

  • Highly twisted bridgehead double bonds correlate with reactivity.
  • A small singlet-triplet energy gap is a key factor for facile cycloaddition.
  • Successful cycloaddition was predicted for ethylene, acetylene, perfluoroethylene, and cyclooctyne.

Conclusions:

  • Anti-Bredt alkenes with specific structural and electronic properties can undergo [2 + 2] cycloadditions.
  • These findings offer insights into the synthesis of four-membered rings.