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Videos de Conceptos Relacionados

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.6K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
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...
4.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
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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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Reacción Aza-Quasi-Favorskii: Construcción de aziridinas altamente sustituidas a través de un proceso concertado de

Padmanabha V Kattamuri1, Jidong Zhao1, Tamal Kanti Das1

  • 1Department of Chemistry, Rice University, Houston, Texas 77030, United States.

Journal of the American Chemical Society
|June 8, 2022
PubMed
Resumen

Un nuevo reordenamiento aza-cuasi-Favorskii permite la síntesis de aziridinas complejas. Esta reacción dominó involucra oximas y enolados de O-sulfonilo, confirmados por estudios computacionales de la vía nitrenoide.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética

Sus antecedentes:

  • Las aziridinas son heterociclos valiosos que contienen nitrógeno con amplias aplicaciones en química medicinal y ciencias de los materiales.
  • La construcción eficiente de aziridinas altamente sustituidas sigue siendo un desafío sintético.

Objetivo del estudio:

  • Desarrollar una nueva metodología sintética para acceder a las aziridinas altamente sustituidas.
  • Para investigar el mecanismo de la nueva reacción de reordenamiento.

Principales métodos:

  • Reacción de oximas de O-sulfonilo deficientes en electrones con enolados derivados de acetofenona disueltos en alfa.
  • Utilizando un proceso de reacción de dominó.
  • Estudios computacionales en profundidad (por ejemplo, DFT) para dilucidar el mecanismo de reacción.

Principales resultados:

  • El desarrollo exitoso de la reorganización aza-Quasi-Favorskii.
  • Se obtuvieron altos rendimientos de diversas aziridinas altamente sustituidas.
  • Los estudios computacionales revelaron una vía de reordenamiento de tipo nitrenoide asíncrona pero concertada.

Conclusiones:

  • El reordenamiento aza-cuasi-Favorskii proporciona una ruta eficiente para las aziridinas altamente sustituidas.
  • La reacción procede a través de un mecanismo único de reordenamiento de nitrenoides.
  • Esta metodología amplía el conjunto de herramientas para la síntesis de aziridina.