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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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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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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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3.5K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Activación intramolecular Csp3-H en un centro de platino resultante de la activación O2: el papel de un ligando

Juan Rueda-Espinosa1,2, Wen Zhou1, Jennifer A Love1,2

  • 1Department of Chemistry, University of Calgary, 2500 University Dr. NW, Calgary, Alberta T2N 1N4, Canada.

Journal of the American Chemical Society
|December 4, 2024
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio revela nuevos complejos de platino (IV) formados por oxidación aeróbica de un precursor de platino (II). Detalla el primer estudio mecanicista de la activación de Csp3-H en los centros de platino.

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Área de la Ciencia:

  • Química organometálica
  • Catalización de platino
  • Mecanismos de reacción

Sus antecedentes:

  • Los complejos de platino (II) son ampliamente estudiados, pero su oxidación a platino (IV) puede producir diversos productos.
  • Las vías de oxidación estándar para los complejos de platino (II) con ligandos quelatantes de N,N están bien establecidas.
  • La activación de C-H es una transformación crucial en la química organometálica, particularmente para los centros metálicos de alta valencia.

Objetivo del estudio:

  • Para investigar los productos de la oxidación aeróbica de un complejo de dimetil-platino-II con un ligando de 1,1-di-2-piridil-etanol.
  • Para aclarar el mecanismo de la inesperada formación del complejo de platino.
  • Proporcionar el primer estudio mecanicista de la activación de Csp3-H en un centro de platino.

Principales métodos:

  • Oxidación aeróbica del precursor del dimetilplatino.
  • Caracterización de los complejos de platino resultantes.
  • Estudios mecanicistas que incluyen complejos de modelos y cálculos de la Teoría Funcional de Densidad (DFT).

Principales resultados:

  • Formación de dos complejos inesperados de platino (IV) en una proporción de 1: 1, que difieren de los productos de oxidación típicos.
  • Identificación de un producto con un centro de platino isomerizado y un modo de coordinación kappa-N,N,O.
  • Descubrimiento del segundo producto resultante de la activación intramolecular del fragmento metilo del ligando, que implica una activación C-H similar a la desprotonación por metalización concertada (CMD) en Pt (IV).

Conclusiones:

  • La naturaleza sensible a los protones del ligando 1,1-di(2-piridil) etanol es crítica para la formación de intermedios de reacción únicos.
  • Este trabajo presenta la primera investigación mecanicista de la activación de Csp3-H en un centro de platino.
  • Los hallazgos amplían la comprensión de la química de la oxidación del platino y los mecanismos de activación de C-H.