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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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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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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.2K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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3.6K
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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3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.5K
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6.2K
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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Cobalt-Catalyzed Wagner-Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination.

Reece H Hoogesteger1, Nicola Murdoch1, David B Cordes1

  • 1EaStCHEM, School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK.

Angewandte Chemie (International Ed. in English)
|July 6, 2023
PubMed
Summary

Cobalt catalysis enables a Wagner-Meerwein rearrangement in allylarenes, producing valuable fluoroalkanes. This novel method achieves high yields, showcasing a unique pathway for electrophilic fluorination and aryl migration.

Keywords:
CationsCobalt CatalysisHydrofluorinationPhenonium IonWagner-Meerwein

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Fluorination Chemistry

Background:

  • Wagner-Meerwein rearrangement is a key carbocation intermediate reaction.
  • Hydrofluorination often involves harsh conditions or lacks selectivity.
  • Developing efficient catalytic methods for selective fluorination is crucial in organic synthesis.

Purpose of the Study:

  • To develop a novel cobalt-catalyzed method for Wagner-Meerwein rearrangement of gem-disubstituted allylarenes.
  • To investigate the mechanism of fluoroalkane formation via nucleophilic fluorination.
  • To demonstrate the unique capability of cobalt catalysis in promoting 1,2-aryl migration.

Main Methods:

  • Utilizing a cobalt catalyst for the rearrangement of gem-disubstituted allylarenes.
  • Employing N-fluoropyridinium oxidants with modifications to the counteranion.
  • Comparing the reaction outcome with other metal-mediated hydrofluorination procedures.

Main Results:

  • Achieved isolated yields of fluoroalkane products up to 84%.
  • Evidence suggests nucleophilic fluorination occurs during the reaction, influenced by the oxidant's counteranion.
  • Other hydrofluorination methods failed to induce the observed 1,2-aryl migration.

Conclusions:

  • Cobalt catalysis uniquely facilitates Wagner-Meerwein rearrangement in allylarenes, leading to fluoroalkanes.
  • The reaction proceeds through a reactive electrophilic intermediate generated under these specific catalytic conditions.
  • This methodology offers a new synthetic route for accessing complex fluorinated organic molecules.