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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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Oxidation and Reduction of Organic Molecules01:19

Oxidation and Reduction of Organic Molecules

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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...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

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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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Preparation of Epoxides03:00

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
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Oxymercuration-Reduction of Alkenes02:36

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Oxenoids in organic synthesis.

Yury Minko1, Ilan Marek

  • 1The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion - Israel Institute of Technology, Haifa 320008, Israel. chilanm@tx.technion.ac.il.

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Metalated peroxides act as effective oxenoids for selective oxidation of organometallic compounds. This review highlights their key applications in modern organic synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Oxidation Reactions

Background:

  • Metalated peroxides possess unique electronic properties.
  • These compounds function as potent oxenoids (electrophilic oxidants).

Purpose of the Study:

  • To review the prominent applications of metalated peroxides in organic synthesis.
  • To showcase their utility in selective oxidation processes.

Main Methods:

  • Experimental studies on metalated peroxides.
  • Theoretical investigations of their reactivity.
  • Compilation of key synthetic applications.

Main Results:

  • Metalated peroxides enable highly selective oxidation of nucleophilic organometallic species.
  • Demonstrated efficiency in various organic transformations.
  • Unique reactivity profile as electrophilic oxidants.

Conclusions:

  • Metalated peroxides are valuable reagents for efficient and selective oxidations.
  • Their application in organic synthesis is expanding.
  • Further exploration of their synthetic potential is warranted.