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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.4K
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.
15.4K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.7K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.4K
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...
3.4K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

9.8K
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.
9.8K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.8K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.8K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
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...
4.0K

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Updated: Jun 12, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Halogenation-enabled intramolecular deaminative cyclization.

Wenbo Wang1, Gang He1,2

  • 1State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. hegang@nankai.edu.cn.

Organic & Biomolecular Chemistry
|May 19, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a novel halogenation method to activate typically inert carbon-nitrogen bonds. This breakthrough enables efficient amine transformations through intramolecular substitution reactions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Carbon-nitrogen (C-N) bonds are generally unreactive to nucleophilic substitution.
  • Developing new methods for C-N bond activation is crucial for synthetic chemistry.

Purpose of the Study:

  • To present a novel halogenation-induced strategy for activating C-N bonds.
  • To demonstrate an efficient method for amine transformation via intramolecular substitution.

Main Methods:

  • Employing a halogenation-induced approach to activate C-N bonds.
  • Facilitating intramolecular nucleophilic substitution reactions.

Main Results:

  • Successfully activated inert C-N bonds using halogenation.
  • Achieved intramolecular substitution of secondary and tertiary amines by hydroxyl, amino, carboxyl, or thiol groups.
  • Developed an efficient protocol for amine transformation.

Conclusions:

  • The presented halogenation strategy offers a new pathway for C-N bond activation.
  • This method provides an efficient route for diverse amine transformations.