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Preparation of Epoxides

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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

11.1K
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Síntesis de éter programable habilitada por la reacción de Oxa-Matteson

Qiqiang Xie1, Guangbin Dong1

  • 1Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.

Journal of the American Chemical Society
|May 9, 2022
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron una nueva reacción de oxa-Matteson para la síntesis orgánica. Este método permite la inserción secuencial de oxígeno y carbenoides en los boronatos, creando diversos éteres sustituidos por boro para la construcción de moléculas complejas.

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Área de la Ciencia:

  • Química orgánica
  • Metodología sintética
  • Química del boro

Sus antecedentes:

  • Las reacciones de tipo Matteson son valiosas para construir moléculas orgánicas complejas a través de estrategias sintéticas iterativas.
  • Las reacciones actuales de tipo Matteson se basan principalmente en la homologación de cadenas de carbono, lo que limita su alcance.
  • Existe la necesidad de nuevos métodos sintéticos que amplíen la diversidad de las arquitecturas moleculares accesibles.

Objetivo del estudio:

  • Desarrollar una nueva reacción de oxa-Matteson para la síntesis de éteres sustituidos por boro.
  • Para permitir la inserción secuencial de oxígeno y carbenoides en varios alquilboronatos y arilboronatos.
  • Demostrar la utilidad de la nueva reacción en la síntesis de éteres funcionales y moléculas complejas.

Principales métodos:

  • Desarrollo de la reacción oxa-Matteson que involucra inserciones secuenciales de oxígeno y carbenoides.
  • Aplicación de la reacción a diversos alquilboronatos y arilboronatos.
  • Demostración de la utilidad sintética mediante la preparación de éteres funcionales, un inhibidor de la acetil-CoA-carboxilasa y poliéteres.

Principales resultados:

  • Desarrollo exitoso de la reacción oxa-Matteson, expandiendo el alcance de la química tipo Matteson.
  • Síntesis eficiente de una amplia gama de éteres sustituidos por boro.
  • Utilidad demostrada en la síntesis asimétrica y la construcción programable de poliéteres.

Conclusiones:

  • La reacción oxa-Matteson proporciona una entrada distinta y versátil a los éteres sustituidos por boro.
  • Esta nueva metodología amplía significativamente la aplicabilidad de las reacciones de tipo Matteson en la síntesis orgánica.
  • La reacción es una herramienta poderosa para la síntesis de moléculas funcionales y poliéteres complejos.