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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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

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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: 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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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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[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.
14.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.4K
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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Tetramethyleneethane Equivalents: Recursive Reagents for Serialized Cycloadditions.

Paul A Wender1, Matthew S Jeffreys1, Andrew G Raub1

  • 1Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, United States.

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Researchers developed novel reagents that enable sequential [4 + 2] cycloadditions, efficiently building complex molecules. This discovery offers a step-economical approach for synthesizing valuable compounds like pharmaceuticals and materials.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Achieving structural complexity efficiently requires reactions forming multiple bonds per step.
  • Diels-Alder and metal-catalyzed cycloadditions are powerful but often require sequential operations.
  • There is a need for reagents that amplify complexity generation in a single operation.

Purpose of the Study:

  • To introduce a new class of reagents capable of recursive cycloadditions.
  • To demonstrate the utility of these reagents in synthesizing complex carbo- and heterobicyclic structures.
  • To apply this methodology to the synthesis of a novel solvatochromic fluorophore.

Main Methods:

  • Synthesis of the parent recursive reagent, 2,3-dimethylene-4-trimethylsilylbutan-1-ol (DMTB), via olefin metathesis.
  • Utilizing DMTB in sequential Diels-Alder and metal-catalyzed [4 + 2] cycloadditions.
  • Triggering a vinylogous Peterson elimination to regenerate a diene for a second cycloaddition.

Main Results:

  • The developed reagents facilitate back-to-back [4 + 2] cycloadditions in a single catalytic cascade.
  • This multicomponent reaction efficiently produces diverse carbo- and heterobicyclic building blocks.
  • Successful three-step synthesis of the solvatochromic fluorophore 6-DMA was achieved.

Conclusions:

  • The new recursive reagents offer a powerful strategy for rapid complexity generation in organic synthesis.
  • This approach provides step-, time-, cost-, and waste-economy in synthesizing valuable molecules.
  • The methodology is applicable to the creation of natural products, therapeutic leads, imaging agents, and materials.