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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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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: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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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Interconversión reversible de macrociclo a macrociclo impulsada por la selección del disolvente

Fei Wang1, Xiangling Shi1, Yi Zhang1

  • 1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China.

Journal of the American Chemical Society
|May 12, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron una nueva síntesis de una sola olla para macrociclos autoensamblados. La elección del disolvente controla la formación de productos macrocíclicos de diferentes tamaños, lo que permite interconversiones reversibles entre las estructuras [1 + 1] y [2 + 2].

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Área de la Ciencia:

  • Química supramolecular
  • Síntesis orgánica
  • Ciencias de los materiales

Sus antecedentes:

  • Las interconversiones de macrociclo a macrociclo ofrecen diversas posibilidades estructurales.
  • El logro de interconversiones controladas y reversibles entre macrociclos de diferentes tamaños presenta un desafío significativo.

Objetivo del estudio:

  • Desarrollar una síntesis fácil de un solo recipiente para macrociclos autoensamblados.
  • Investigar el control del tamaño del macrociclo y la interconversión mediante la manipulación del disolvente.

Principales métodos:

  • Reacciones de condensación entre los dialdehídos oligopirrólicos α,α'-enlazados y las alquildiaminas.
  • Utilización de varios disolventes (metanol, etanol, cloroformo, DMSO, DMF, MeCN) para influir en la distribución del producto.
  • Caracterización de los productos macrocíclicos (conjuntos [1 + 1] y [2 + 2]).

Principales resultados:

  • Un dialdehído oligopirrólico con puente de piridina (3) y las diaminas alquilo forman fácilmente macrociclos [2 + 2], independientemente del disolvente.
  • La condensación de 3 con 2,2'-oxibis ((etilamina) 14) da como resultado macrociclos [1 + 1] o [2 + 2] según la elección del disolvente.
  • Los disolventes específicos (metanol, etanol, cloroformo) favorecen los productos [1 + 1], mientras que otros (DMSO, DMF, MeCN) favorecen los productos [2 + 2], a menudo como precipitados.
  • La interconversión reversible entre los macrociclos [1 + 1] y [2 + 2] se puede lograr alterando el disolvente, impulsado por factores termodinámicos y de solubilidad.

Conclusiones:

  • Se ha establecido un método versátil de un solo recipiente para sintetizar macrociclos autoensamblados.
  • Se demuestran las interconversiones de macrociclos reversibles controladas por solventes, que ofrecen una nueva estrategia para la diversidad estructural.
  • Los hallazgos ponen de relieve la importancia de los parámetros termodinámicos y de solubilidad para dirigir los procesos de autoensamblaje.