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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Oxidation of Phenols to Quinones01:17

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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.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Dynamic Hydroxyl-Yne Reaction with Phenols.

Tanausú Santos1, Yaiza Pérez-Pérez2, David S Rivero2

  • 1Instituto Universitario de Bio-Orgánica Antonio González (IUBO), Universidad de La Laguna, P.O. Box 456, 38206 La Laguna, Tenerife, Spain.

Organic Letters
|November 9, 2022
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Summary
This summary is machine-generated.

Dynamic Covalent Chemistry now includes a new fast and reversible reaction between phenols and vinyl ethers. This discovery enables the creation of novel responsive materials and molecular cages under mild conditions.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Dynamic Covalent Chemistry (DCvC) is crucial for creating adaptable molecular systems.
  • Existing DCvC reactions often require specific conditions or lack broad applicability.

Purpose of the Study:

  • To introduce and validate a new dynamic covalent exchange reaction between phenols and vinyl ethers.
  • To explore the kinetics and thermodynamics of this novel reaction.
  • To demonstrate its utility in synthesizing advanced materials.

Main Methods:

  • Investigated the reaction kinetics and thermodynamics of phenol-vinyl ether exchange.
  • Utilized computational methods to calculate equilibrium constants.
  • Employed the reaction for the synthesis of a responsive molecular cage.

Main Results:

  • Confirmed the dynamic and reversible nature of the phenol-vinyl ether exchange.
  • Demonstrated that the exchange is rapid at room temperature and under mild conditions.
  • Quantified the influence of phenol substituents on the reaction equilibrium.
  • Successfully synthesized a responsive molecular cage using this new DCvC methodology.

Conclusions:

  • The phenol-vinyl ether exchange represents a significant and versatile addition to the Dynamic Covalent Chemistry toolbox.
  • This reaction's mild conditions and speed make it highly attractive for supramolecular chemistry and materials science.
  • The successful synthesis of a responsive molecular cage highlights the practical applicability of this new chemical transformation.