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Videos de Conceptos Relacionados

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.7K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
2.7K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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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...
2.3K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

3.3K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
3.3K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.2K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
13.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.3K
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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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Metátesis de olefinas catalíticas E selectivas controladas cinéticamente

Thach T Nguyen1, Ming Joo Koh1, Xiao Shen1

  • 1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.

Science (New York, N.Y.)
|April 30, 2016
PubMed
Resumen

Los investigadores desarrollaron nuevos métodos de metátesis de olefinas para una síntesis eficiente de los isómeros E. Este avance proporciona acceso directo a los valiosos cloruros de E-alquenilo y fluoruros mediante el uso de catalizadores de molibdeno.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis estereoselectiva

Sus antecedentes:

  • La metátesis de olefinas es crucial en química, pero carece de métodos eficientes para favorecer cinéticamente los isómeros E.
  • La generación de isómeros E termodinámicamente desfavorecidos sigue siendo un desafío importante en la química sintética.

Objetivo del estudio:

  • Desarrollar nuevas reacciones de metástasis cruzada cinéticamente selectivas.
  • Para permitir la síntesis eficiente de cloruros de E-alquenilo termodinámicamente desfavorecidos y fluoruros con alta estereoselectividad.

Principales métodos:

  • Se utilizó un catalizador a base de molibdeno (1,05,0 mol%) suministrado en gránulos de parafina estables.
  • Reacciones de metástasis cruzadas a temperatura ambiente, generalmente completadas en un plazo de 4 horas.

Principales resultados:

  • Se obtienen altos rendimientos y una estereoselectividad excepcional para los cloruros de E-alquenilo y los fluoruros.
  • Se ha demostrado la accesibilidad directa y fácil a los cloruros de E-alquenilo de pureza isomérica.
  • Ha sintetizado con éxito fluoruros de E-alquenilo de moléculas simples y complejas.

Conclusiones:

  • El método desarrollado supera las limitaciones en la metástasis de olefinas, permitiendo la E-selectividad cinética.
  • Proporciona una vía versátil para haluros de E-alquenilo valiosos para futuras transformaciones químicas.
  • Facilita la síntesis de compuestos biológicamente relevantes que contienen fracciones de E-alquenilo.