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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
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
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.6K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.5K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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EnT触媒を利用したラジカルリレーカスケード環化による多置換シクロヘキサン/シクロヘキセンへのアクセス

Mei Xiang1, Cong Huang1, Jie Gao1

  • 1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China. hyangchem@csu.edu.cn.

Chemical communications (Cambridge, England)
|December 24, 2025
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まとめ

可視光媒介性の三重項-三重項エネルギー移動（EnT）触媒は、多置換シクロヘキサンおよびシクロヘキセン骨格の効率的な合成を可能にします。この新しいラジカルリレー環化戦略は、広範な基質適用範囲と高いジアステレオ選択性のために二官能性試薬を利用しています。

キーワード:
可視光触媒エネルギー移動触媒ラジカル反応環化反応シクロヘキサン誘導体シクロヘキセン誘導体

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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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Last Updated: Jan 8, 2026

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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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科学分野:

  • 有機化学
  • 触媒
  • 光化学

背景:

  • 可視光光触媒は急速に成長している分野です。
  • 三重項-三重項エネルギー移動（EnT）触媒は、独自の反応性経路を提供します。
  • 複雑な環状骨格を合成するための効率的な方法を開発することは非常に重要です。

研究 の 目的:

  • 新しいEnT触媒ラジカルリレー環化戦略を開発すること。
  • 多様な多置換シクロヘキサンおよびシクロヘキセン骨格を合成すること。
  • 合理的に設計された二官能性試薬の有用性を探求すること。

主な方法:

  • 可視光照射。
  • 三重項-三重項エネルギー移動（EnT）触媒。
  • ラジカルリレー環化。
  • 新規二官能性試薬：ジフェニルメタンo-(2,2-ジメチル-4-フェニルペンタ-4-エニル)オキシムを使用しました。

主要な成果:

  • 様々な多置換シクロヘキサンおよびシクロヘキセン骨格の合成に成功しました。
  • アルケンおよびアルキンを用いた広範な基質適用範囲を実証しました。
  • 環化反応において優れたジアステレオ選択性を達成しました。
  • シクロヘキサン生成物の6-アザビシクロ[3.2.1]オクタン-7-オン誘導体への容易な変換を示しました。

結論:

  • 開発されたEnT触媒ラジカルリレー環化は、簡潔かつ効果的な方法です。
  • 二官能性試薬は、効率的な変換のための二重ラジカル前駆体として機能します。
  • このアプローチは、複雑な環状分子への環境に優しいルートを提供します。