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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Updated: Jun 13, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Aryl-bromide reductive elimination from an isolated Pt(IV) complex.

Anette Yahav-Levi1, Israel Goldberg, Arkadi Vigalok

  • 1School of Chemistry, The Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.

Chemical Communications (Cambridge, England)
|April 20, 2010
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a platinum(IV) complex that selectively eliminates a bromoarene molecule. Mechanistic studies reveal the reaction pathway for this novel platinum chemistry.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Reaction Mechanisms

Background:

  • Platinum complexes are crucial in catalysis and medicine.
  • Understanding ligand elimination is key to controlling reactivity.
  • Platinum(IV) chemistry offers unique reaction pathways.

Purpose of the Study:

  • To synthesize and characterize a novel platinum(IV) complex.
  • To investigate the mechanism of selective bromoarene elimination.
  • To explore the reactivity of platinum(IV) complexes with aryl and bromo ligands.

Main Methods:

  • Synthesis of the platinum(IV) complex.
  • Full spectroscopic characterization (NMR, Mass Spectrometry, X-ray crystallography).
  • Kinetic studies to elucidate the reaction mechanism.

Main Results:

  • Successful preparation and characterization of the Pt(IV) complex.
  • Demonstration of selective elimination of a bromoarene molecule.
  • Detailed mechanistic insights into the elimination pathway.

Conclusions:

  • The novel Pt(IV) complex exhibits unique reactivity.
  • Selective bromoarene elimination is a viable reaction pathway.
  • This study contributes to the understanding of platinum(IV) reaction mechanisms.