Jove
Visualize
お問い合わせ
JoVE
x logofacebook logolinkedin logoyoutube logo
JoVEについて
概要リーダーシップブログJoVEヘルプセンター
著者向け
出版プロセス編集委員会範囲と方針査読よくある質問投稿
図書館員向け
推薦の声購読アクセスリソース図書館諮問委員会よくある質問
研究
JoVE JournalMethods CollectionsJoVE Encyclopedia of Experimentsアーカイブ
教育
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab Manual教員リソースセンター教員サイト
利用規約
プライバシーポリシー
ポリシー

関連する概念動画

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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).
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

こちらも読む

関連記事

共著者、ジャーナル、引用グラフによってこの研究に関連する記事。

並び替え
Same author

Anionic Polymerization of O‑Benzyl and O-<i>tert-</i>Butyldimethylsilyl Dienes Derived from Myrcene to Yield Functional Polyenes.

ACS omega·2026
Same author

Electronic Spin State Determines Bidirectional Catalysis of Dual-Atom Catalysts in Sulfur Cathodes.

ACS applied materials & interfaces·2026
Same author

Dynamic Microinterfacial Polymerization Enables Scalable Synthesis of Two-Dimensional Polymer Sheets for Quasi-Solid-State Electrolytes in Sodium-Metal Batteries.

Angewandte Chemie (International ed. in English)·2026
Same author

Self-Healing and Reprocessable Soft Robots Using 3D Digital Light Printing.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2025
Same author

Büchner Ring Expansion/Isomerization: Photoactivation of Imide-Annulated N-Heterocyclic Carbenes Affords Vicinal Diamino Cycloheptatrienes.

Organic letters·2025
Same author

Hyaluronic Acid-Functionalized Highly Porous Polymeric Materials for Stem Cell Culture.

Chemistry of materials : a publication of the American Chemical Society·2025
Same journal

Gas-Responsive Metal-Organic Frameworks for Adaptive Thermal Energy Storage with Tunable Charge-Discharge Temperatures.

Journal of the American Chemical Society·2026
Same journal

Engineering a Thiamine-Dependent Benzoylformate Decarboxylase for Stereodivergent Radical C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Bond Formation.

Journal of the American Chemical Society·2026
Same journal

Accelerated Directional Proton-Coupled Electron Transfer Enabled by Intrinsic Dipole Field in Biomimetic α-Helical Structure.

Journal of the American Chemical Society·2026
Same journal

Alternating Current-Driven Hydrogen Isotope Labeling of Aliphatic Amines Using 1,3-Propanedithiol as an Efficient Hydrogen Atom Transfer Reagent.

Journal of the American Chemical Society·2026
Same journal

Two-Dimensional van der Waals Polar Metal MoOBr<sub>2</sub>.

Journal of the American Chemical Society·2026
Same journal

Negatively Curved Chiral Bilayer Nanographene.

Journal of the American Chemical Society·2026
関連記事をすべて見る

関連する実験動画

Updated: Jun 2, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

機械的に促進されたレトロ [4+2] サイクル添加

Kelly M Wiggins1, Jay A Syrett, David M Haddleton

  • 1Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.

Journal of the American Chemical Society
|April 21, 2011
PubMed
まとめ
この要約は機械生成です。

機械的な力は,レトロサイクロアディションによるポリマーチェーン分裂を誘発する. 挿入されたアダクトを持つポリメチルアクリラートに適用された超音波は,この反応を開始し,新しいメカノケミカル経路を示した.

さらに関連する動画

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

関連する実験動画

Last Updated: Jun 2, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

科学分野:

  • ポリマー化学のポリマー化学について
  • メカノ化学 メカノ化学
  • マテリアルサイエンス 材料科学

背景:

  • ポリマー鎖は,サイクロアディション反応を用いて機能化することができる.
  • 機械化学反応は,ポリマー改変のための新しい経路を提供します.

研究 の 目的:

  • ポリマーにおけるレトロ [4+2] サイクロアディション反応の機械的活性化を調査する.
  • 超音波で誘発されたポリマーチェーン分裂を調査するために.

主な方法:

  • 組み込まれている [4+2] サイクロアディション添加物を持つポリー (((メチルアクリラート)) の合成.
  • 低温でのポリマーの超音波処理.
  • ゲル浸透クロマトグラフィー (GPC) と紫外線スペクトロスコーピーを用いた分析.
  • クロモフォールで解放された部分のラベル付け.

主要な成果:

  • M (n) >30 kDaのポリマーにおける超音波誘導レトロ [4+2]サイクル添加.
  • 機械的に活性化されたレトロサイクル添加率は,アントラセンの添加物を用いて測定した.
  • 鎖分裂と分子の解放は,アダクトの位置とポリマーの分子量に依存していた.

結論:

  • ポリマーチェーンに埋め込まれたサイクロアディションアダクトは,機械的な力に敏感です.
  • 矢量的に対極の機械的な力は,レトロサイクル加算を活性化するための鍵です.
  • この研究は,機械化学によるポリマー鎖分裂のための新しい方法を示しています.