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Related Concept Videos

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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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

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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...
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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.
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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.
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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 acids to...
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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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Au-Catalysed oxidative cyclisation.

Zhitong Zheng1, Zhixun Wang1, Youliang Wang1

  • 1Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA. zhang@chem.ucsb.edu.

Chemical Society Reviews
|January 20, 2016
PubMed
Summary
This summary is machine-generated.

This tutorial explores two gold-catalyzed oxidative cyclization strategies. One uses nucleophilic oxidants to form reactive intermediates, while the other involves Au(i)/Au(iii) redox catalysis for synthetic transformations.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Gold catalysis offers unique reactivity for organic synthesis.
  • Oxidative cyclization is a key transformation for constructing complex molecules.

Purpose of the Study:

  • To provide a tutorial on the two main strategies for gold-catalyzed oxidative cyclization.
  • To highlight the mechanistic pathways and synthetic applications of these methods.

Main Methods:

  • Discussion of strategies involving nucleophilic oxidants (internal/external).
  • Explanation of gold(I)/gold(III) redox catalysis with external oxidants.
  • Illustrative examples of synthetic transformations enabled by these methods.

Main Results:

  • The first strategy utilizes the weak O-heteroatom bond in oxidants to generate reactive gold carbene intermediates.
  • The second strategy employs an external oxidant to drive a catalytic cycle involving changes in gold's oxidation state.
  • Both strategies have been successfully applied to diverse synthetic challenges.

Conclusions:

  • Gold-catalyzed oxidative cyclization presents powerful and versatile synthetic routes.
  • Understanding these distinct strategies enhances the development of novel organic transformations.