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Related Concept Videos

Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.0K
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...
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

4.5K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
4.5K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

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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...
3.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.2K
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...
4.2K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.8K
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.
6.8K

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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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Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group*.

Guillaume Force1, Anna Perfetto2, Robert J Mayer3

  • 1Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), CNRS UMR 8182, Université Paris-Saclay, Bâtiment 420, 91405, Orsay, France.

Angewandte Chemie (International Ed. in English)
|July 2, 2021
PubMed
Summary

Researchers developed a novel macrolactonization method using a pentafluorophenyl mixed anhydride. This effective and versatile strategy provides convenient access to diverse macrolactones, macrodiolides, and esters for chemical and pharmaceutical applications.

Keywords:
hydroxyacidsmacrocyclizationmacrodiolidesmacrolactonesmixed anhydride

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Macrolactones are crucial in pharmaceuticals and fine chemicals.
  • Existing macrolactonization methods lack efficiency, selectivity, or functional group compatibility.
  • A need exists for improved synthetic strategies for macrolactone synthesis.

Purpose of the Study:

  • To develop a novel and versatile macrolactonization promoter system.
  • To enable efficient synthesis of macrolactones, macrodiolides, and esters.
  • To investigate the mechanism of the novel promoting system.

Main Methods:

  • Formation of a mixed anhydride intermediate containing a pentafluorophenyl group.
  • Application of the mixed anhydride in macrolactonization reactions.
  • Kinetic studies and Density Functional Theory (DFT) computations.

Main Results:

  • The pentafluorophenyl mixed anhydride system demonstrated high effectiveness and versatility.
  • The method provides convenient access to a broad range of macrolactones, macrodiolides, and esters.
  • Reactivity was rationalized through kinetic and computational analyses.

Conclusions:

  • The developed strategy offers a valuable new tool for macrolactone synthesis.
  • This method addresses limitations of previous macrolactonization techniques.
  • The findings contribute to advancing synthetic organic chemistry and drug discovery.