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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

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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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Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts
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A Hafnium-Substituted Lindqvist Polyoxotungstate: Synthesis, Characterization, and Catalysis of H2O2-Based

Vasilii Yu Evtushok1, Olga V Zalomaeva1, Nataliya V Maksimchuk1

  • 1Boreskov Institute of Catalysis SB RAS, Acad. Lavrentiev Ave. 5, 630090 Novosibirsk, Russia.

Inorganic Chemistry
|April 18, 2026
PubMed
Summary

Hafnium-substituted dimeric polyoxotungstates ({HfW5}2) show improved catalytic activity in hydrogen peroxide (H2O2)-based oxidations compared to their zirconium analogues ({ZrW5}2). The Hf-based catalyst demonstrates a higher oxidation rate and reduced H2O2 dismutation.

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Molten-Salt Synthesis of Complex Metal Oxide Nanoparticles
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Molten-Salt Synthesis of Complex Metal Oxide Nanoparticles
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Molten-Salt Synthesis of Complex Metal Oxide Nanoparticles

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Area of Science:

  • Inorganic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Lindqvist-type dimeric polyoxotungstates are versatile catalysts for oxidation reactions.
  • Zirconium-substituted analogues have shown promise, but their performance can be further optimized.
  • Exploring substitution with other early transition metals like hafnium is crucial for catalyst development.

Purpose of the Study:

  • To synthesize and characterize a novel hafnium-substituted Lindqvist-type dimeric polyoxotungstate, ({HfW5}2).
  • To compare the catalytic performance of {HfW5}2 with its zirconium analogue ({ZrW5}2) in H2O2-based oxidations.
  • To investigate the impact of metal substitution (Hf vs. Zr) on catalytic activity and selectivity.

Main Methods:

  • Synthesis of {HfW5}2 and {ZrW5}2 polyoxotungstates.
  • Characterization using single-crystal and powder X-ray diffraction, elemental analysis, TGA, FTIR, NMR (17O, 183W), and HR-ESI-MS.
  • Catalytic testing in thioanisole oxidation and singlet oxygen probe reactions using aqueous H2O2.

Main Results:

  • {HfW5}2 was successfully synthesized and characterized, exhibiting a structure similar to {ZrW5}2.
  • {HfW5}2 demonstrated a ~5-fold higher rate for thioanisole oxidation compared to {ZrW5}2.
  • {HfW5}2 showed a lower rate of unproductive H2O2 dismutation and modest yields in singlet oxygen probe reactions compared to {ZrW5}2.

Conclusions:

  • Replacing Zr(IV) with the more oxophilic Hf(IV) in Lindqvist tungstates significantly enhances catalytic performance in H2O2-based oxidations.
  • The Hf-analogue offers improved efficiency and selectivity in specific oxidation pathways.
  • This study highlights the potential of Hf-substituted polyoxotungstates as advanced oxidation catalysts.