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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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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...
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Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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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.
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Radical Substitution: Allylic Bromination01:27

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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...
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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.
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Bromobenzene Transforms Lanthanoid Pseudo-Grignard Chemistry.

Md Abdul Halim1, Zhifang Guo1, Glen B Deacon2

  • 1College of Science & Engineering, James Cook University, Townsville, 4811, Qld, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 18, 2023
PubMed
Summary

New divalent lanthanoid pseudo-Grignard reagents (PhLnBr) react with bulky ligands to form unique bromine-bridged dimers and monomeric complexes. These findings offer new synthetic pathways for lanthanoid chemistry.

Keywords:
Pseudo-Grignard reagentsbromine-bridge dimerscrystal structureseuropiumlanthanoid(II) complexesoxidative additionsamariumytterbium

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Area of Science:

  • Organometallic Chemistry
  • Lanthanoid Chemistry
  • Coordination Chemistry

Background:

  • Lanthanoid pseudo-Grignard reagents offer unique reactivity.
  • Previous studies with PhLnI provided different outcomes.
  • The synthesis of novel lanthanoid complexes is of significant interest.

Purpose of the Study:

  • To synthesize and characterize new divalent lanthanoid complexes using PhLnBr reagents.
  • To investigate the reactivity of PhLnBr with bulky N,N'-bis(2,6-di-isopropylphenyl)formamidine (DippFormH) and 3,5-diphenylpyrazole (Ph2pzH).
  • To compare the structural and coordination properties of the resulting complexes.

Main Methods:

  • Preparation of divalent lanthanoid pseudo-Grignard reagents (PhLnBr) via oxidative addition of bromobenzene to lanthanoid metals in THF.
  • Reaction of PhLnBr with DippFormH and Ph2pzH.
  • Characterization of the resulting lanthanoid complexes, including structural determination (e.g., coordination number, dimeric/monomeric nature).

Main Results:

  • Successful synthesis of bromine-bridged dimeric complexes [Ln(DippForm)Br(thf)3]2·6thf (Sm, Eu) and [Yb(DippForm)Br(thf)2]2·2thf.
  • Formation of both divalent [Eu(Ph2pz)2(thf)4] and trivalent [Sm(Ph2pz)3(thf)3]·3thf, [Sm(Ph2pz)3(dme)2]·dme complexes.
  • Observed differences in coordination numbers (seven for Sm/Eu, six for Yb in dimers; nine for Sm, eight for Eu in monomers).

Conclusions:

  • PhLnBr reagents provide a versatile route to novel divalent lanthanoid complexes.
  • The choice of ligand (DippFormH vs. Ph2pzH) influences the structure and oxidation state of the resulting lanthanoid complexes.
  • These findings expand the synthetic toolbox for lanthanoid organometallic chemistry, offering different outcomes compared to PhLnI reagents.