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Related Concept Videos

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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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.5K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.5K
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

4.6K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
4.6K
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

8.2K
Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.8K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Orthogonal Thiol Addition Chemistry Based on Ether Acrylates.

Linh Duy Thai1, Marco Neumaier1, Christopher Barner-Kowollik1,2,3,4

  • 1Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.

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Researchers developed a new method for creating advanced materials using ether acrylates. This approach achieves true orthogonality in chemical reactions, enabling precise synthesis of complex polymers and photoswitches with tailored properties.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Thiol-Michael and radical thiol-ene reactions are key for soft matter synthesis.
  • A major challenge is the lack of orthogonality between acrylates and electron-rich olefins in radical thiol-ene reactions.

Purpose of the Study:

  • To achieve true orthogonality between activated double bonds in polymer synthesis.
  • To develop a method for synthesizing sequence-defined macromolecular photoswitches and brush-like polymers.

Main Methods:

  • Utilized ether acrylates (β-alkoxyacrylates) synthesized via hydroxyl-yne click reaction.
  • Exploited the radical inactivity of ether acrylates to control reaction pathways.

Main Results:

  • Achieved true orthogonality between activated double bonds.
  • Successfully synthesized difficult-to-prepare sequence-defined main-chain macromolecular photoswitches.
  • Synthesized brush-like polymers with controlled architectures.

Conclusions:

  • Ether acrylates enable precise control over thiol-ene and thiol-Michael reactions.
  • This strategy provides a straightforward route to advanced materials with tunable properties.
  • Opens new avenues for designing complex macromolecular architectures.