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Related Concept Videos

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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.
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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Alternating Current-Driven Diol Epimerization via a Deplete-Regenerate Strategy.

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
Summary
This summary is machine-generated.

This study introduces alternating-current (AC) electrolysis for electrocatalytic epimerization, overcoming redox incompatibilities. A novel deplete-regenerate strategy temporally separates redox events, enabling efficient stereochemical editing of complex molecules.

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Area of Science:

  • Organic Chemistry
  • Electrosynthesis
  • Stereochemistry

Background:

  • Epimerization is crucial for accessing under-represented stereoisomers without changing molecular structure.
  • Existing photocatalytic methods are available, but electrocatalytic epimerization is limited by redox incompatibilities under direct current (DC) electrolysis.

Purpose of the Study:

  • To develop a general electrocatalytic epimerization method.
  • To overcome the limitations of DC electrolysis for simultaneous oxidation and reduction.

Main Methods:

  • Utilized alternating-current (AC) electrolysis for electrocatalytic epimerization.
  • Employed a deplete-regenerate strategy with a thiol mediator.
  • Separated redox events temporally through polarity reversal.

Main Results:

  • Achieved general electrocatalytic epimerization using AC electrolysis.
  • Demonstrated a deplete-regenerate mechanism for temporal separation of redox events.
  • Showcased compatibility with diverse functional groups and complex bioactive molecules.

Conclusions:

  • AC electrolysis provides a novel solution for electrocatalytic epimerization by resolving redox incompatibilities.
  • The developed method enables efficient stereochemical editing through time-separated redox processes.
  • This approach expands the toolkit for synthesizing valuable isomers and complex molecules.