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Related Concept Videos

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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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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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.
13.7K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

18.4K
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

8.1K
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

3.1K
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...
3.1K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Selective Alcohol Oxidation by a Copper TEMPO Catalyst: Mechanistic Insights by Simultaneously Coupled Operando

Jabor Rabeah1, Ursula Bentrup2, Reinhard Stößer3

  • 1Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany). jabor.rabeah@catalysis.de.

Angewandte Chemie (International Ed. in English)
|July 16, 2015
PubMed
Summary

This study introduces a novel operando spectroscopy setup for gas-liquid reactions. The findings reveal TEMPO stabilizes a key intermediate in copper-catalyzed benzyl alcohol oxidation, challenging prior redox mechanism assumptions.

Keywords:
TEMPOUV/Vis spectroscopyalcohol oxidationhomogeneous catalysisoperando spectroscopy

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Area of Science:

  • Catalysis
  • Spectroscopy
  • Reaction Mechanisms

Background:

  • Copper and TEMPO (2,2,6,6-tetramethylpiperidin-1-yl)oxyl are widely used catalysts for oxidation reactions.
  • Understanding the precise reaction mechanisms, especially in gas-liquid phases, remains challenging.
  • Previous mechanistic proposals for copper/TEMPO catalysis require further investigation.

Purpose of the Study:

  • To present the first coupled operando Electron Paramagnetic Resonance (EPR)/UV-Visible (UV-Vis)/Attenuated Total Reflectance Infrared (ATR-IR) spectroscopy setup.
  • To investigate the mechanism of copper/TEMPO-catalyzed oxidation of benzyl alcohol using this new technique.
  • To elucidate the role of TEMPO in the catalytic cycle.

Main Methods:

  • Development and application of a coupled operando EPR/UV-Vis/ATR-IR spectroscopy system.
  • Gas-liquid phase reaction studies.
  • Mechanistic investigation of benzyl alcohol oxidation catalyzed by copper and TEMPO.

Main Results:

  • The study successfully applied the novel operando spectroscopy setup to copper/TEMPO-catalyzed benzyl alcohol oxidation.
  • No direct redox reaction between TEMPO and Cu(I)/Cu(II) was detected, contradicting some previous hypotheses.
  • Evidence suggests TEMPO stabilizes a key intermediate: (bpy)(NMI)Cu(II)-O2(⋅-)-TEMPO.

Conclusions:

  • The developed coupled operando spectroscopy system is effective for studying gas-liquid phase reaction mechanisms.
  • The proposed mechanism involving TEMPO stabilization of a copper-dioxygen-TEMPO intermediate offers a new perspective on copper/TEMPO catalysis.
  • This work provides crucial insights into the mechanistic pathways of important oxidation reactions.