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Videos de Conceptos Relacionados

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
4.0K
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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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.8K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

3.0K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
3.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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.
3.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Reacciones de Indol Dieromativo (3 + 2) con Cationes Azaoxalilo - Nuevo Método para la Síntesis de las

Maria C DiPoto1, Russell P Hughes1, Jimmy Wu1

  • 1Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.

Journal of the American Chemical Society
|November 13, 2015
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce una nueva síntesis de pirroloindolinas mediante reacciones de anulación dearomativa. El análisis computacional revela un mecanismo escalonado, con disolventes como TFE y HFIP que mejoran las tasas de reacción a través del enlace de hidrógeno.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética
  • Química computacional

Sus antecedentes:

  • Las pirroloindolinas son una clase significativa de compuestos heterocíclicos que contienen nitrógeno.
  • Las rutas sintéticas eficientes para las pirroloindolinas son cruciales para la química medicinal y la ciencia de los materiales.

Objetivo del estudio:

  • Informar sobre la primera síntesis de pirroloindolinas mediante la anulación dearomativa (3 + 2).
  • Para elucidar el mecanismo de reacción utilizando métodos computacionales.
  • Investigar el papel de los disolventes en la mejora de la velocidad de reacción.

Principales métodos:

  • Reacción de anulación dearomativa entre los indolos 3-sustituidos y los cationes azaoxalilo.
  • Cálculos de la teoría funcional de la densidad (DFT) (B3LYP-D3/6-311G**) para estudiar la vía de reacción.
  • Análisis de la estabilización del estado de transición mediante enlaces de hidrógeno.

Principales resultados:

  • Se ha demostrado la síntesis exitosa de pirroloindolinas.
  • Un mecanismo de reacción gradual que implica la formación inicial de enlaces C-C en el indol C3 seguido por el cierre del anillo fue apoyado por DFT.
  • Se demostró que los disolventes como TFE y HFIP estabilizan los estados de transición, aumentando las tasas de reacción.

Conclusiones:

  • La anulación dearomativa (3 + 2) proporciona una nueva vía para la síntesis de pirroloindolina.
  • Los cálculos de DFT ofrecen información mecanicista valiosa, lo que pone de relieve la importancia de los efectos del solvente.
  • Este trabajo allana el camino para un mayor desarrollo de estrategias aromáticas en la síntesis orgánica.