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Electrophiles02:28

Electrophiles

13.2K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Carbocations02:10

Carbocations

14.3K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.9K
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,...
2.9K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

12.4K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Updated: Mar 13, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Electrophilic phenoxy-substituted phosphonium cations.

James H W LaFortune1, Timothy C Johnstone1, Manuel Pérez1

  • 1Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, CanadaM5S 3H6. dstephan@chem.utoronto.ca.

Dalton Transactions (Cambridge, England : 2003)
|October 28, 2016
PubMed
Summary

New electrophilic phosphonium salts were synthesized and tested for air stability. Their Lewis acidity was evaluated computationally and experimentally in various catalytic reactions, showing promise for chemical synthesis.

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

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Area of Science:

  • Organophosphorus chemistry
  • Electrophilic chemistry
  • Catalysis

Background:

  • Phosphonium salts are versatile compounds in organic synthesis.
  • Electrophilicity and Lewis acidity are key properties determining reactivity.
  • Understanding these properties is crucial for designing new catalysts and reagents.

Purpose of the Study:

  • To synthesize and characterize a new family of phenoxy-substituted phosphonium salts.
  • To evaluate the air stability of these novel compounds.
  • To compare their electrophilicity and Lewis acidity using computational and experimental methods.

Main Methods:

  • Synthesis of [(RO)P(C6F5)3][B(C6F5)4] phosphonium salts with varying R groups (phenyl, 4-fluorophenyl, 2,4-difluorophenyl, pentafluorophenyl).
  • Assessment of air stability through observation and testing.
  • Computational studies including fluoride ion affinity and global electrophilicity index calculations.
  • Experimental evaluation of Lewis acidity in reactions like Friedel-Crafts dimerization, hydrodefluorination, hydrosilylation, hydrodeoxygenation, and dehydrocoupling.

Main Results:

  • Successful synthesis of a series of electrophilic phenoxy-substituted phosphonium salts.
  • Evaluation of their air stability.
  • Correlation between computational electrophilicity indices and experimental Lewis acidity.
  • Demonstration of catalytic activity in various transformations indicating Lewis acidity.

Conclusions:

  • The synthesized phosphonium salts exhibit tunable electrophilicity and Lewis acidity.
  • These compounds show good air stability, making them practical reagents.
  • The study provides insights into structure-reactivity relationships for electrophilic phosphonium salts.
  • Potential applications in catalysis and organic synthesis are highlighted.