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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

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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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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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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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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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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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Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition
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Artificial Metallooxidases from Cyclodextrin Diacids.

Bo Wang1, Mikael Bols1

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen O, Denkmark.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 1, 2017
PubMed
Summary
This summary is machine-generated.

Simple artificial metalloenzymes were created using cyclodextrin diacids. These novel catalysts efficiently mediated oxidation reactions, showing significant rate accelerations for benzylic alcohols.

Keywords:
biomimetic synthesiscyclodextrinsironkineticsoxidation

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Biomimetic Chemistry

Background:

  • Artificial metalloenzymes offer tunable catalytic properties.
  • Cyclodextrins are versatile host molecules with potential for functionalization.

Purpose of the Study:

  • To synthesize and characterize novel artificial metalloenzymes based on cyclodextrin diacids.
  • To investigate the metal-binding properties and catalytic activity of these new systems.

Main Methods:

  • Synthesis of six α- and β-cyclodextrin diacids.
  • Metal complexation studies with copper, zinc, and iron.
  • Evaluation of catalytic activity in Fenton-like oxidation of benzylic alcohols.

Main Results:

  • Stable metal complexes (dissociation constants 0.4–8×10⁻⁴ M) were formed with Cu, Zn, and Fe.
  • Iron complexes catalyzed Fenton-like oxidation of benzylic alcohols.
  • Catalysis followed Michaelis-Menten kinetics with rate accelerations up to 2700-fold.

Conclusions:

  • Cyclodextrin diacids provide a simple and effective platform for creating artificial metalloenzymes.
  • These novel metalloenzymes demonstrate significant catalytic efficiency in oxidation reactions.