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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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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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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

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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 carbon to...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Preparation of Diols and Pinacol Rearrangement01:57

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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.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Mecanismo de la formación de indoles catalizados por Rh2: el catalizador no controla la selectividad del producto

Jason G Harrison1, Osvaldo Gutierrez1, Navendu Jana2

  • 1Department of Chemistry, University of California-Davis , 1 Shields Avenue, Davis, California 95616, United States.

Journal of the American Chemical Society
|January 1, 2016
PubMed
Resumen

Los estudios computacionales exploraron la síntesis de indol promovida por Rh a partir de vinilo / azidoarenos. Un mecanismo propuesto muestra que el catalizador Rh facilita la generación de nitrógeno pero no participa en el paso de ciclización.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química computacional

Sus antecedentes:

  • Los derivados del indole son cruciales en los productos farmacéuticos y la ciencia de los materiales.
  • Las rutas sintéticas eficientes para los indoles son muy buscadas.
  • La catálisis del rodio (Rh) ofrece potencial para nuevas metodologías sintéticas.

Objetivo del estudio:

  • Para aclarar el mecanismo de la formación de indolos promovida por Rh.
  • Para investigar el papel del catalizador Rh en la vía de reacción.
  • Proponer un modelo mecánico detallado para la transformación.

Principales métodos:

  • Se emplearon cálculos de la Teoría Funcional de la Densidad (DFT).
  • Las vías de reacción y los estados de transición se analizaron computacionalmente.
  • Las superficies de energía potencial se mapearon para comprender la dinámica de la reacción.

Principales resultados:

  • Se identificó un mecanismo de reacción plausible.
  • Se descubrió que el catalizador Rh promueve la generación de un intermediario clave de nitreno.
  • El catalizador Rh no estuvo directamente involucrado en la siguiente etapa de ciclización.

Conclusiones:

  • El mecanismo propuesto proporciona información sobre la síntesis de indol catalizada por Rh.
  • Comprender el papel del catalizador puede guiar el desarrollo de sistemas catalíticos más eficientes.
  • Este estudio contribuye al conocimiento fundamental de la catálisis organometálica y la química orgánica sintética.