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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Halogens03:01

Halogens

22.4K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Related Experiment Video

Updated: Nov 30, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Organocatalyzed Fluoride Metathesis.

Daniel Mulryan1, Andrew J P White1, Mark R Crimmin1

  • 1Department of Chemistry, Molecular Sciences Research Hub, Imperial College London, White City, Shepherds Bush, London W12 0BZ, United Kingdom.

Organic Letters
|November 17, 2020
PubMed
Summary
This summary is machine-generated.

A novel organocatalyzed reaction enables fluoride exchange in organic molecules. This method efficiently manipulates fluorine content, offering a new pathway for synthesizing fluorinated compounds with high atom economy.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Area of Science:

  • Organic Chemistry
  • Organocatalysis
  • Fluorine Chemistry

Background:

  • Fluorine-containing organic molecules are crucial in pharmaceuticals and materials science.
  • Developing efficient methods for introducing and manipulating fluorine atoms is a key challenge in organic synthesis.

Purpose of the Study:

  • To report a new organocatalyzed reaction for fluoride metathesis.
  • To demonstrate a novel approach for manipulating the fluorine content in organic molecules.

Main Methods:

  • Development of an organocatalyzed reaction between fluoroarenes and carbonyl derivatives.
  • Investigation of fluoride (F-) exchange with various nucleophiles (e.g., acetate, chloride, cyanide).

Main Results:

  • Successful fluoride metathesis reaction achieved using organocatalysis.
  • Demonstrated exchange of fluoride with multiple nucleophiles.
  • Achieved a byproduct-free and 100% atom-efficient reaction by integrating fluorination and defluorination into a single catalytic cycle.

Conclusions:

  • The reported reaction offers a conceptually novel strategy for fluorine manipulation in organic synthesis.
  • This method provides an efficient and sustainable route to fluorinated organic compounds.