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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
1.9K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.6K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
5.6K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
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9.3K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
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9.3K

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Structural verification and new reactivity for Stang's reagent, [PhI(CN)][OTf].

Jason D Bennetts1, Lachlan Barwise1, Lachlan Sharp-Bucknall1

  • 1Department of Chemistry, La Trobe University, La Trobe Institute for Molecular Science, Melbourne, Victoria, Australia. j.dutton@latrobe.edu.au.

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|June 16, 2023
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Summary

Stang's reagent, an ion-pair in solution, acts as a strong Lewis acid. It oxidizes pyridine ligands to form new CDAP reagent derivatives, useful for polysaccharide activation.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Stang's reagent [PhI(CN)][OTf] is a hypervalent iodine compound.
  • Its structural and chemical properties in organic solution require further elucidation.

Purpose of the Study:

  • To confirm the structure of Stang's reagent using X-ray crystallography.
  • To investigate its behavior as a Lewis acid and its reactivity with pyridine ligands.

Main Methods:

  • X-ray crystallography for structural determination.
  • Spectroscopic analysis to characterize reaction products.
  • Lewis acid-base interaction studies.

Main Results:

  • The structure of Stang's reagent is confirmed as an ion-pair in organic solution.
  • Stang's reagent exhibits strong Lewis acidity.
  • Reaction with pyridine yields [Pyr-CN][OTf] salts via pyridine oxidation.

Conclusions:

  • Stang's reagent exists as an ion-pair in solution.
  • The reagent's Lewis acidity leads to the formation of novel pyridine derivatives.
  • These derivatives represent new analogs of the CDAP reagent, applicable in polysaccharide activation.