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関連する概念動画

Sharpless Epoxidation02:57

Sharpless Epoxidation

3.8K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
3.8K
Preparation of Epoxides03:00

Preparation of Epoxides

7.4K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.4K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.6K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.6K
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.1K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.8K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

8.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
8.2K

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関連する実験動画

Updated: May 30, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

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コバルト-TAML触媒による電気化学的に誘導された選択的オレフィンエポキシデーション

Suyeon S Kim1, Sugyeong Hong2, Adarsh Koovakattil Surendran3

  • 1Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, South Korea.

Journal of the American Chemical Society
|January 29, 2025
PubMed
まとめ

この研究では,コバルト-テトラアミドマクロサイクルリガンド ([CoIII(TAML) ]-) の触媒を用いた新しい電気触媒エポキシデーションを導入した. この持続可能な方法は,水を酸素源として使用して,環境条件下でオレフィンをエポキシドに効率的に変換します.

さらに関連する動画

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

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関連する実験動画

Last Updated: May 30, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
09:21

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

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科学分野:

  • 緑の化学
  • カタリシス
  • 電気化学

背景:

  • エポキシドの熱化学変換は,厳しい環境と温室効果ガスの排出を含む課題に直面しています.
  • エポキシドは様々な工業製品の製造に不可欠な中間物質です.
  • エポキシド合成のための持続可能な代替手段の開発は不可欠です.

研究 の 目的:

  • オレフィンエポキシデーションの代替で持続可能な電気触媒方法の開発
  • 効率的で選択的なエポキシデーションのために,分子触媒 [CoIII(TAML) ]- を利用する.
  • 反応メカニズムを調査し,活性中間物質を特定する.

主な方法:

  • [CoIII(TAML) ]-触媒を用いた電解エポキシデーション
  • 環境条件下で酸素原子源として水を利用する.
  • 電動力学研究,オペランド電圧測定-電圧噴射電離質量測定 (VESI-MS),および電子パラマグネティック共鳴 (EPR) を使って,機械的洞察を得ました.

主要な成果:

  • [CoIII(TAML) ]-触媒は,サイクロヘクセンエポキシデーションに対して高い選択性 (> 90%) とファラダイク効率 (> 60%) を示した.
  • 触媒はオレフィンエポキシデーションのための幅広い基板範囲を示した.
  • 速度を制限するステップとして,陽子結合電子移転プロセスが識別され,反応性コバルト-酸素種が形成された.

結論:

  • [CoIII(TAML) ]-触媒は,従来の熱化学的エポキシデーションに効率的で持続可能な代替手段を提供します.
  • この電気触媒的アプローチは 価値ある化学原料の生産に 新しい経路を提供する.
  • この発見は,電気化学的方法を用いたよりグリーンな化学合成の道を開く.