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Related Concept Videos

Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

12.0K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

21.0K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
21.0K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.9K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.9K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.4K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.4K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.9K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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A General Copper-Catalyzed Vinylic Halogen Exchange Reaction.

Antoine Nitelet1, Gwilherm Evano1

  • 1Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles (ULB) , Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.

Organic Letters
|April 1, 2016
PubMed
Summary

A new method efficiently converts alkenyl iodides to chlorinated and brominated compounds using copper iodide catalysis. This halogen exchange reaction preserves double bond geometry and offers a versatile route to valuable alkenyl halides.

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Area of Science:

  • Organic Chemistry
  • Halogen Exchange Reactions
  • Catalysis

Background:

  • Alkenyl halides are important synthetic intermediates.
  • Efficient methods for halogen exchange in alkenyl halides are limited.
  • Synthesis of chlorinated and brominated alkenyl derivatives is challenging.

Purpose of the Study:

  • To develop an efficient and general system for halogen exchange in alkenyl halides.
  • To synthesize chlorinated and brominated alkenyl derivatives from readily available alkenyl iodides.
  • To investigate the scope and limitations of the developed reaction.

Main Methods:

  • Reaction of alkenyl iodides with tetramethylammonium chloride or bromide.
  • Use of catalytic amounts of copper iodide and trans-N,N'-dimethylcyclohexane-1,2-diamine.
  • Optimization of reaction conditions for yield and selectivity.

Main Results:

  • A wide range of alkenyl iodides were smoothly transformed into chlorinated and brominated derivatives.
  • Excellent yields and full retention of double bond geometry were achieved.
  • The reaction was effective for chlorination of bromoalkenes and applicable to gem-dibromoalkenes.

Conclusions:

  • An efficient and general halogen exchange system for alkenyl halides has been established.
  • The developed method provides a versatile route to valuable chlorinated and brominated alkenyl compounds.
  • The reaction offers high yields and preserves stereochemistry, making it valuable for organic synthesis.