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Preparation of Epoxides03:00

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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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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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Acid-Catalyzed Ring-Opening of Epoxides02:24

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Preparation of Alkynes: Alkylation Reaction02:27

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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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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Síntesis de γ-lactamas por anulación intermolecular (3 + 2) de las silosialquinas y de las 3-aminooxetanas

Xiang Li1, Qiang Feng2, Shuxuan Liu1

  • 1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, China.

Precision chemistry
|August 29, 2025
PubMed
Resumen

Una nueva reacción catalizada por plata sintetiza eficientemente γ-butirolactamas a partir de siloxialquinas y 3-aminooxetanos. Este método ofrece una ruta suave y selectiva a valiosos compuestos de lactamo.

Palabras clave:
(3 + 2) Anulación3-Aminooxetano y sus derivadosAnulación de un acuerdoSiloxialquina y sus derivadosG-lactamo y sus derivados

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Los γ-butirolactamos son motivos estructurales importantes en los productos farmacéuticos y naturales.
  • El desarrollo de rutas sintéticas eficientes y selectivas para los lactamos funcionalizados sigue siendo un desafío clave en la síntesis orgánica.

Objetivo del estudio:

  • Desarrollar una nueva reacción de anulación catalizada por plata para la síntesis de γ-butirolactamos.
  • Explorar el alcance y el mecanismo de la reacción utilizando siloxialquinas y 3-aminooxetanos.

Principales métodos:

  • Utilizando la catálisis de plata para una reacción de anulación intermolecular (3 + 2).
  • Utilizando siloxialquinas y 3-aminooxetanos como materiales de partida.
  • Investigar las condiciones de reacción para optimizar el rendimiento y la selectividad.

Principales resultados:

  • Desarrollo exitoso de una anulación (3 + 2) catalizada por plata de los alquinos siloxi y los 3-aminooxetanos.
  • Se ha logrado una alta regioselectividad y estereoselectividad en la formación de γ-butirolactamas.
  • Demostró un procedimiento sintético suave y conveniente.

Conclusiones:

  • La anulación catalizada por plata desarrollada proporciona un método eficaz para acceder a los γ-butirolactamos.
  • La reacción procede a través de la formación de un enlace C-N intermolecular seguido de la apertura del anillo de oxetano.
  • Esta metodología ofrece una herramienta valiosa para la síntesis de estructuras complejas de lactamo.