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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Halogens03:01

Halogens

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.
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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A generic route to fluoroalkyl-containing phosphanes.

Alan K Brisdon1, Christopher J Herbert

  • 1School of Chemistry, The University of Manchester, Manchester, UK M13 9PL. alan.brisdon@manchester.ac.uk

Chemical Communications (Cambridge, England)
|October 30, 2009
PubMed
Summary

Trimethylsilyl-containing phosphanes react with perfluoroiodoalkanes, offering a straightforward method for synthesizing perfluoroalkyl-containing phosphanes. This research presents a versatile route for creating novel fluorinated phosphorus compounds.

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Area of Science:

  • Organophosphorus Chemistry
  • Fluorine Chemistry

Background:

  • Perfluoroalkyl-containing phosphanes are valuable building blocks in materials science and medicinal chemistry.
  • Existing synthetic routes may be limited in scope or require harsh conditions.

Purpose of the Study:

  • To develop a general and convenient synthetic method for perfluoroalkyl-containing phosphanes.
  • To explore the reaction between trimethylsilyl-containing phosphanes and perfluoroiodoalkanes.

Main Methods:

  • Reaction of trimethylsilyl-containing phosphanes with various perfluoroiodoalkanes.
  • Purification and characterization of the resulting perfluoroalkyl-containing phosphanes using standard analytical techniques (e.g., NMR, Mass Spectrometry).

Main Results:

  • The reaction successfully yielded a range of perfluoroalkyl-containing phosphanes.
  • The method proved to be general, accommodating different perfluoroalkyl chain lengths and phosphane structures.
  • High yields and convenient isolation of the products were observed.

Conclusions:

  • The reaction of trimethylsilyl-containing phosphanes with perfluoroiodoalkanes is an effective and accessible route to perfluoroalkyl-containing phosphanes.
  • This method provides a valuable tool for the synthesis of fluorinated organophosphorus compounds.