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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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La activación de hidrógeno por un trifoshabenzeno aromático.

Lauren E Longobardi1, Christopher A Russell, Michael Green

  • 1Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

Journal of the American Chemical Society
|August 29, 2014
PubMed
Resumen

Los heterociclos aromáticos ahora se pueden reducir sin catalizadores. Un nuevo 1,3,5-trifoshabenzeno se somete a hidrogenación directa, obteniendo productos únicos de biciclo-reducción a través de un mecanismo de formación de enlaces P-P.

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Área de la Ciencia:

  • Química organometálica Química orgánica de los metales.
  • La catálisis es la catálisis.
  • Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

  • La hidrogenación aromática generalmente requiere condiciones duras o catalizadores metálicos.
  • El desarrollo de métodos de reducción más suaves y libres de metales es un desafío clave en la síntesis orgánica.

Objetivo del estudio:

  • Para investigar la hidrogenación directa de los heterociclos aromáticos.
  • Explorar el mecanismo de la reducción aromática no catalizada mediante el uso de 2,4,6-tri-tert-butil-1,3,5-trifoshabenzeno.

Principales métodos:

  • Hidrogenación bajo presión leve (4 atm H2).
  • Elucidación de la estructura mediante cristalografía de rayos X y espectroscopia de RMN.
  • Estudios mecánicos que emplean experimentos de para-hidrógeno y cálculos de la Teoría Funcional de Densidad (DFT).

Principales resultados:

  • El 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene se reduce a productos biciclo bajo 4 atm H2 sin catalizadores.
  • La reacción procede a través de adición reversible de 1,4-H2 y un desplazamiento de hidruro superficial irreversible con formación de enlace P-P.
  • Los cálculos de DFT revelan que la fácil distorsión de una configuración de barco facilita la reducción no catalizada.

Conclusiones:

  • La hidrogenación aromática directa y no catalizada se puede lograr utilizando heterociclos aromáticos específicos.
  • El mecanismo de reacción implica cambios conformacionales únicos y la formación de enlaces P-P.
  • Este descubrimiento ofrece una nueva vía para la reducción sin metales de sistemas aromáticos.