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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

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A Technical Guide for Performing Spectroscopic Measurements on Metal-Organic Frameworks
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Recent Advances in Direct Single Oxygen Atom Insertion Into Organic Frameworks.

Qixue Qin1,2,3, Zihan Wu3, Yanjie Li2

  • 1School of Chemistry and Chemical Engineering, University of Jinan, Jinan, China.

Chemistry, an Asian Journal
|July 3, 2026
PubMed
Summary

Single-atom skeletal editing precisely modifies molecules by inserting oxygen atoms into carbon-carbon or carbon-heteroatom bonds. This review details key strategies and reaction classes for advancing synthetic chemistry.

Keywords:
mechanismorganic frameworkoxygen atom insertionoxygen‐containing compoundskeletal editing

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Single-atom skeletal editing offers precise molecular framework modification.
  • Oxygen atom incorporation significantly impacts molecular properties and reactivity.
  • Traditional synthesis methods face challenges in accessing complex molecular structures.

Purpose of the Study:

  • To review progress in single-atom skeletal editing focusing on oxygen atom insertion.
  • To delineate primary reaction classes: C─C and C─X bond oxygenation.
  • To provide a practical guide and inspire future innovations in molecular synthesis.

Main Methods:

  • Review of diverse oxygen insertion strategies.
  • Analysis of strain-driven cleavage mechanisms.
  • Evaluation of functional group-directed activation and photoelectrochemical methods.
  • Examination of hypervalent iodine-mediated rearrangements.

Main Results:

  • Categorization of oxygen insertion into C─C and C─X bonds.
  • Critical evaluation of various synthetic strategies, mechanisms, scopes, and applications.
  • Identification of key advancements in single-atom skeletal editing.

Conclusions:

  • Oxygen atom insertion is a powerful tool in single-atom skeletal editing.
  • Diverse strategies enable precise control over molecular structure and reactivity.
  • This review serves as a resource for synthetic chemists and researchers.