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Related Concept Videos

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Oxidation of Alcohols02:37

Oxidation of Alcohols

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:
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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...
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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 activated by...

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Published on: February 20, 2020

A Lewis acid promoted oxidative cyclization.

Timothy J Donohoe1, Paul C M Winship, Daryl S Walter

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom. timothy.donohoe@chem.ox.ac.uk

The Journal of Organic Chemistry
|June 22, 2010
PubMed
Summary
This summary is machine-generated.

Replacing trifluoroacetic acid with a Lewis acid catalyst in osmium-mediated oxidative cyclization significantly boosts reaction speed and yield. This method allows for reduced osmium loading and tolerates sensitive protecting groups, improving the overall efficiency of the chemical process.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Osmium-mediated oxidative cyclization is a key reaction in organic synthesis.
  • Traditional methods often require stoichiometric amounts of strong acids like trifluoroacetic acid.
  • These conditions can limit substrate scope due to incompatibility with acid-sensitive functional groups.

Purpose of the Study:

  • To develop a more efficient and milder osmium-mediated oxidative cyclization protocol.
  • To improve reaction yields and rates compared to existing methods.
  • To expand the compatibility of the reaction with acid-sensitive protecting groups.

Main Methods:

  • Utilizing a catalytic amount of Lewis acid instead of trifluoroacetic acid.
  • Performing osmium-mediated oxidative cyclization under mildly acidic conditions.
  • Investigating the effect of reduced osmium loading (as low as 0.2 mol %).

Main Results:

  • Reactions proceeded nearly an order of magnitude faster.
  • Higher yields were achieved compared to previous methods.
  • The protocol demonstrated tolerance for a wide range of acid-sensitive protecting groups.

Conclusions:

  • Catalytic Lewis acid mediation offers a superior alternative to trifluoroacetic acid for osmium-mediated oxidative cyclization.
  • This optimized method enhances reaction efficiency, reduces catalyst loading, and broadens substrate scope.
  • The findings provide a more versatile and practical tool for synthetic organic chemists.