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Related Concept Videos

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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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.
2.9K
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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.8K
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.
10.8K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
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.
2.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.1K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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A Modular Cyclopentene Annulation.

Adrian E Samkian1, Kasam Poonswat1, Scott C Virgil1

  • 1Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 101-20, Pasadena, California 91125, United States.

Organic Letters
|May 28, 2025
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Summary

A new three-component reaction efficiently creates highly substituted cyclopentenes using propargyl zinc reagents, dicarbonyls, and electrophiles. This method offers a versatile route for synthesizing complex cyclic compounds.

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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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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Cyclopentene derivatives are important structural motifs in natural products and pharmaceuticals.
  • Efficient and modular synthetic methods are needed for accessing highly substituted cyclopentenes.

Purpose of the Study:

  • To develop a novel three-component annulation strategy for the rapid synthesis of highly substituted cyclopentenes.
  • To explore the scope and limitations of the developed reaction.

Main Methods:

  • Utilized a modular three-component reaction involving propargyl zinc reagents, unsaturated 1,3-dicarbonyls, and various electrophiles.
  • Performed optimization studies to identify optimal reaction conditions.
  • Investigated the substrate scope by employing a range of starting materials.

Main Results:

  • Successfully synthesized a diverse array of highly substituted cyclopentene products.
  • Demonstrated the modularity of the annulation by varying the three coupling partners.
  • Showcased the synthetic utility of the obtained cyclopentenes through subsequent diversification reactions.

Conclusions:

  • The reported three-component annulation provides an efficient and modular approach for constructing highly substituted cyclopentenes.
  • This method offers a valuable tool for synthetic chemists seeking to access complex cyclic structures.
  • The readily diversifiable products highlight the broad applicability of this synthetic strategy.