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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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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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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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Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

2.0K
Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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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.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Updated: Aug 5, 2025

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts
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Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts

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Dioxygen Activation by a Bioinspired Tungsten(IV) Complex.

Miljan Z Ćorović1, Ferdinand Belaj1, Nadia C Mösch-Zanetti1

  • 1Institute of Chemistry, Inorganic Chemistry, University of Graz, 8010 Graz, Austria.

Inorganic Chemistry
|March 29, 2023
PubMed
Summary
This summary is machine-generated.

This study explores tungsten(IV) oxido complexes, which are rare but crucial for biomimetic chemistry. The research details a new tungsten(IV) catalyst that activates dioxygen for oxidation and mimics tungstoenzyme acetylene hydratase activity.

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Biomimetic Chemistry

Background:

  • Tungstoenzymes are vital biological catalysts, driving interest in biomimetic tungsten complexes.
  • Tungsten(VI) dioxido complexes are well-studied, but tungsten(IV) oxido complexes remain underexplored due to challenging reductions.
  • Sulfur-rich ligands are key in bioinspired tungsten chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel phosphine-stabilized tungsten(IV) oxido complex.
  • To investigate the catalytic activity of the tungsten(IV) complex in dioxygen activation and oxidation reactions.
  • To explore the reactivity of the tungsten(IV) complex with acetylene, mimicking tungstoenzyme mechanisms.

Main Methods:

  • Reduction of a tungsten(VI) precursor ([WO2(6-MePyS)2]) using PMe3 to yield the tungsten(IV) complex [WO(6-MePyS)2(PMe3)2].
  • Solution-phase studies to observe ligand dissociation and dioxygen activation by the tungsten(IV) complex.
  • Reaction of the tungsten(IV) complex with acetylene to form a tungsten(IV) acetylene adduct.

Main Results:

  • A stable phosphine-stabilized tungsten(IV) oxido complex was successfully synthesized.
  • The tungsten(IV) complex demonstrated catalytic activity, activating dioxygen for the aerobic oxidation of PMe3.
  • The tungsten(IV) complex formed an acetylene adduct, mimicking the initial step of acetylene hydratase mechanism.

Conclusions:

  • The synthesized tungsten(IV) complex represents a rare example of a stable, catalytically active tungsten(IV) oxido species.
  • This work expands the understanding of tungsten(IV) chemistry and its potential in homogeneous catalysis.
  • The findings provide insights into biomimetic strategies for tungstoenzyme mechanisms, particularly acetylene hydratase.