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Related Concept Videos

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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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).
2.8K
Cycloalkanes02:28

Cycloalkanes

15.2K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
15.2K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
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.
4.1K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.6K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.1K
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.
12.1K
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  11. On-surface Synthesis Of Cyclo[20]carbon And Cyclo[30]carbon From Cyclo[10]carbon

On-surface synthesis of cyclo[20]carbon and cyclo[30]carbon from cyclo[10]carbon

Yuan Guo1, Yuzhe Yun1, Wenzhi Xiang1

  • 1Interdisciplinary Materials Research Center, School of Materials Science and Engineering, Tongji University, Shanghai, 201804, People's Republic of China.

Nature Communications
|December 13, 2025

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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View abstract on PubMed

Summary
This summary is machine-generated.

Researchers synthesized larger cyclocarbons, like C20 and C30, by coupling and ring-opening smaller C10 cyclocarbons. This new method overcomes precursor challenges for creating larger carbon rings and may enable controlled polymerization.

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • On-surface synthesis has produced cyclo[n]carbons (Cn) up to C26 using designed precursors.
  • Synthesizing precursors for larger cyclocarbons remains a significant challenge.

Purpose of the Study:

  • To develop a new strategy for synthesizing larger cyclocarbons.
  • To overcome limitations in precursor synthesis for extended carbon rings.

Main Methods:

  • Utilized C10 cyclocarbons as precursors.
  • Employed scanning tunneling microscope tip manipulation to induce coupling and ring-opening reactions.
  • Characterized the synthesized molecules using bond-resolved atomic force microscopy.

Main Results:

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  • Successfully synthesized C20 and C30 cyclocarbons from C10 precursors.
  • Unambiguously confirmed the polyynic structure of C30, consistent with theoretical predictions.
  • Demonstrated a novel pathway for accessing larger cyclocarbons.

    • Conclusions:

    • Established a new synthetic route for larger cyclocarbons via coupling and ring-opening of smaller ones.
    • This approach offers a potential method for the controlled polymerization of cyclocarbons.
    • Overcomes challenges associated with precursor synthesis for large cyclo[n]carbons.