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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

2.8K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
2.8K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

2.6K
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.
2.6K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.3K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.3K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.1K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.1K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

5.2K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
5.2K
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

2.1K
As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
2.1K

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Quinol-Enedione Rearrangement.

Tomás Vieira de Castro1, François Richard1, Steven H Bennett1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, U.K.

Organic Letters
|April 30, 2025
PubMed
Summary

The quinol-enedione rearrangement efficiently synthesizes 2-cyclohexene-1,4-diones from para-quinols. Optimized conditions and mechanistic insights expand its synthetic utility for complex molecules.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The quinol-enedione rearrangement is a method for synthesizing 2-cyclohexene-1,4-diones.
  • Early reports on this transformation were sporadic, lacking optimization and scope investigation.

Purpose of the Study:

  • To optimize reaction conditions for the quinol-enedione rearrangement.
  • To systematically investigate the substrate scope of the reaction.
  • To explore the synthetic potential of the enedione products.

Main Methods:

  • Optimization of Brønsted acid-mediated reaction conditions.
  • Systematic investigation of various para-quinol substrates.
  • Demonstration of kinetic selectivity between competing rearrangements.
  • Exploration of product transformations using various synthetic methods.

Main Results:

  • Optimized Brønsted acid-mediated conditions were established for the synthesis of 2-cyclohexene-1,4-diones.
  • A wide range of substituted and unsubstituted quinol derivatives were found to be suitable substrates.
  • Kinetic selectivity favoring the desired quinol-enedione rearrangement over the dienone-phenol rearrangement was achieved.
  • The enedione products were successfully transformed into complex polycyclic structures.

Conclusions:

  • The quinol-enedione rearrangement is a valuable synthetic tool, optimized for efficiency and scope.
  • The study provides a framework for applying this rearrangement in organic synthesis.
  • Computational studies offer mechanistic insights into the rearrangement process.