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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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Keto–Enol Tautomerism: Mechanism01:14

Keto–Enol Tautomerism: Mechanism

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The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed conditions. Both the reactions involve the same steps—protonation and deprotonation— although in the reverse order.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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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Preparation of Epoxides03:00

Preparation of Epoxides

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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...
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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Reactivity of Enols01:18

Reactivity of Enols

3.3K
Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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Updated: Sep 11, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Annulative endoperoxidation of tetronates.

Najmeh Rahimi1, Saba Sehrish1, Samuel K Akompong1

  • 1Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM, USA. rtelloab@nmsu.edu.

Organic & Biomolecular Chemistry
|August 14, 2025
PubMed
Summary

Researchers developed a new annulative endoperoxidation for tetronate derivatives. This method efficiently produces tricyclic endoperoxides under mild conditions using a simple setup.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Tetronate derivatives are important organic compounds.
  • Endoperoxidation reactions are valuable for synthesizing complex molecules.

Purpose of the Study:

  • To present a novel annulative endoperoxidation of tetronate derivatives.
  • To explore a new synthetic route for tricyclic endoperoxides.

Main Methods:

  • Utilizing tetronate derivatives with unsaturated side chains.
  • Employing a simple reaction setup under mild conditions.

Main Results:

  • Successful generation of tricyclic endoperoxides.
  • Achieved modest diastereoselectivities and useful yields.
  • Proposed a free-radical mechanism for the reaction.

Conclusions:

  • The developed endoperoxidation is an efficient method for synthesizing tricyclic endoperoxides.
  • The reaction proceeds under accessible and mild conditions.
  • The proposed free-radical mechanism provides insight into the reaction pathway.