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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: 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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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

7.0K
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...
7.0K
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

5.8K
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...
5.8K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

13.2K
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.
13.2K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.9K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations.

Tobias Stopka1, Meike Niggemann1, Nuno Maulide2

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Angewandte Chemie (International Ed. in English)
|August 24, 2017
PubMed
Summary

This study presents a metal-free method for creating α-carbonyl cations from alkynes. These reactive intermediates enable the synthesis of complex molecules with congested carbon centers in one step.

Keywords:
oxidative cyclizationrearrangementsulfoxidesvinyl cationsα-carbonyl cations

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Metal-free synthetic strategies are crucial for sustainable chemistry.
  • Vinyl cations are important intermediates in organic synthesis.

Purpose of the Study:

  • To develop a selective, metal-free method for generating α-carbonyl cations.
  • To explore the reactivity of these cations in complex molecule synthesis.

Main Methods:

  • Addition of sulfoxides to densely substituted vinyl cations.
  • Mechanistic analysis to understand reaction pathways.

Main Results:

  • Successful generation of α-carbonyl cations from simple internal alkynes.
  • Demonstrated high reactivity leading to hydrogen and carbon shifts with unusual selectivities.
  • Synthesis of complex compounds with congested tertiary and quaternary carbon centers in a single step.

Conclusions:

  • The developed method provides efficient access to valuable synthetic intermediates.
  • The study offers a predictive scheme for substituent migratory aptitude in these reactions.