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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: 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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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 Alcohols02:37

Oxidation of Alcohols

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

8.0K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
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A solution for 4-propylguaiacol hydrodeoxygenation without ring saturation.

Zihao Zhang1, Qiang Li2, Xiangkun Wu1

  • 1Paul Scherrer Institute, Villigen, 5232, Switzerland.

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Solvent choice significantly impacts lignin upgrading. Tetrahydrofuran (THF) hinders 4-propylguaiacol (4PG) adsorption, favoring demethoxylation over hydrogenation, offering new catalytic control pathways.

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Area of Science:

  • Catalysis
  • Green Chemistry
  • Materials Science

Background:

  • Lignin valorization is crucial for sustainable chemical production.
  • 4-Propylguaiacol (4PG) is a representative lignin-derived monomer.
  • Solvent effects on catalytic hydrodeoxygenation are not fully understood.

Purpose of the Study:

  • To elucidate solvent effects on the hydrodeoxygenation of 4-propylguaiacol (4PG) over a Ru/C catalyst.
  • To understand how different solvents influence reaction pathways and product selectivity.
  • To explore strategies for controlling lignin upgrading processes.

Main Methods:

  • Operando synchrotron photoelectron photoion coincidence (PEPICO) spectroscopy.
  • Molecular dynamics simulations.
  • Catalytic hydrodeoxygenation experiments.

Main Results:

  • Isooctane co-feeding favors ring hydrogenation of 4PG to 2-methoxy-4-propylcyclohexanol due to flat adsorption.
  • Tetrahydrofuran (THF) coordination to the catalyst surface blocks flat adsorption of 4PG.
  • THF promotes demethoxylation to 4-propylphenol and dehydroxylation to propylbenzene.

Conclusions:

  • Solvent choice is a critical factor in directing the hydrodeoxygenation pathway of lignin-derived monomers.
  • THF's interaction with the catalyst surface alters adsorption configurations and suppresses hydrogenation.
  • Tailoring solvent properties offers a promising approach for selective lignin upgrading.