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Related Concept Videos

[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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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.0K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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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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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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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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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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  11. Precise Synthesis Of Pyrene-based Molecular Nanocarbons Driven By Dehydro-diels-alder Reactions

Precise Synthesis of Pyrene-Based Molecular Nanocarbons Driven by Dehydro-Diels-Alder Reactions

Jian Li1, Haohua Chen2,3, Ya Wang1

  • 1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.

Journal of the American Chemical Society
|November 3, 2025

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Preparation of Carbon Nanosheets at Room Temperature
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Preparation of Carbon Nanosheets at Room Temperature

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View abstract on PubMed

Summary
This summary is machine-generated.

Researchers developed a new modular strategy for synthesizing molecular nanocarbons with precise control over their structure. This breakthrough enables the creation of complex carbon architectures for advanced materials and quantum technologies.

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Molecular nanocarbons are crucial intermediates between polycyclic aromatic hydrocarbons and graphene.
  • Precise synthesis of nanocarbons with specific topologies (e.g., K-region, cove-type) is challenging.

Purpose of the Study:

  • To develop a de novo modular synthesis strategy for atomically precise molecular nanocarbons.
  • To enable programmable control over the topology and dimensionality of pyrene-based nanocarbons.

Main Methods:

  • Utilized preorganized aryl acetylnaphthalene precursors and acetylenedicarboxylate for K-region growth.
  • Integrated Suzuki-Miyaura coupling with a Zn(OTf)2-catalyzed cascade reaction.
  • The cascade included Friedel-Crafts alkylation, dehydro-Diels-Alder cycloaddition, and dehydrogenative aromatization.

Related Experiment Videos

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Preparation of Carbon Nanosheets at Room Temperature
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Preparation of Carbon Nanosheets at Room Temperature

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Main Results:

  • Achieved hierarchical construction of pyrene-like structures by inserting naphthalene fragments.
  • Synthesized diverse pyrene-based molecular nanocarbons with linear, contorted, and 3D π-architectures.
  • Demonstrated programmable control over nanocarbon topology and dimensionality.

Conclusions:

  • Established a generalizable blueprint for the bottom-up synthesis of complex carbon-rich architectures.
  • The new strategy overcomes limitations in synthesizing specific nanocarbon topologies with atomic precision.
  • This work advances materials science, optoelectronics, and quantum technologies through precise nanocarbon construction.