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関連する概念動画

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.2K
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.
7.2K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

4.1K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.1K
[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
Preparation of Epoxides03:00

Preparation of Epoxides

9.1K
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 peroxy acids to...
9.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.6K
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.
12.6K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.5K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.5K

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関連する実験動画

Updated: Jan 15, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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枯渇再生戦略による交流電流駆動ダイオルエピメリゼーション

Shaolong Qi1, Duren Yin1, Changqin Huang1

  • 1Shenzhen Grubbs Institute and Department of Chemistry, Guangming Advanced Research Institute, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.

Journal of the American Chemical Society
|October 15, 2025
PubMed
まとめ

この研究では,電気触媒性エピメリゼーションのための交流電流 (AC) 電解を導入し,酸化還元不適合性を克服します. 複雑な分子の効率的な立体化学的編集を可能にします.

さらに関連する動画

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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関連する実験動画

Last Updated: Jan 15, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

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科学分野:

  • 有機化学
  • 電気合成
  • ステレオ化学

背景:

  • エピメリゼーションは,分子構造を変えることなく,不足しているステレオアイソマーにアクセスするために重要です.
  • 既存の光触媒方法は利用可能ですが,電気触媒エピメリゼーションは,直流 (DC) 電解下でのリドックス不適合性によって制限されています.

研究 の 目的:

  • 一般的な電解エピメリゼーション方法を開発する.
  • DC電解の限界を克服し,同時に酸化と還元を行う.

主な方法:

  • 電気触媒によるエピメリゼーションのための交流電流 (AC) 電解を用いる.
  • ティオール媒介剤を用いた枯渇再生戦略を用いた.
  • 極性逆転によって,一時的に分離された酸化還元現象.

主要な成果:

  • AC電解を用いた一般的電気触媒エピメリゼーションを達成した.
  • レドックスイベントの時間分離のための枯渇再生メカニズムを示した.
  • 多様な機能群と複雑な生物活性分子との互換性を示した.

結論:

  • AC電解は,酸化還元不適合性を解消することによって,電気触媒的エピメリゼーションのための新しいソリューションを提供します.
  • 開発された方法は,時間隔離されたリドックスプロセスを通して効率的な立体化学編集を可能にします.
  • このアプローチは,価値ある同位体や複雑な分子を合成するためのツールキットを拡張します.