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Brønsted-Lowry acid-base chemistry is the transfer of protons; thus, logic suggests a relation between the relative strengths of conjugate acid-base pairs. The strength of an acid or base is quantified in its ionization constant, Ka or Kb, which represents the extent of the acid or base ionization reaction. For the conjugate acid-base pair HA / A−, the ionization equilibrium equations and ionization constant expressions are
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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...
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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.
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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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Formación de pares de N/B frustrados reactivos π-conjugados por el reordenamiento de las aminas de propargilo

Tongdao Wang1, Constantin G Daniliuc1, Christian Mück-Lichtenfeld1

  • 1Organisch-Chemisches Institut , Westfälische Wilhelms-Universität Münster , Corrensstraße 40 , 48149 Münster , Germany.

Journal of the American Chemical Society
|February 16, 2018
PubMed
Resumen
Este resumen es generado por máquina.

Se sintetizaron nuevos pares de Lewis frustrados N / B (FLPs) a partir de N-Propargyltetrametilpiperidina y alquenilboranos. Estos FLPs activan el dihidrógeno en condiciones suaves, formando productos de Z-alqueno.

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Área de la Ciencia:

  • Química organometálica
  • Química de las parejas de Lewis

Sus antecedentes:

  • Los pares de Lewis frustrados (FLPs) son clave en la activación de moléculas pequeñas.
  • La reactividad de N/B FLPs con sustratos insaturados es un área de investigación activa.

Objetivo del estudio:

  • Para sintetizar y caracterizar los nuevos pares de Lewis N/B frustrados con puentes de alquenilo.
  • Investigar la reactividad de estos FLPs hacia la activación de dihidrógeno.

Principales métodos:

  • Reacción de la N-Propargyltetrametilpiperidina con los compuestos trans-alquenil-B ((C6F5) 2).
  • Caracterización espectroscópica (NMR, difracción de rayos X) de los productos.
  • Reacciones de división de dihidrógeno y cálculos de DFT.

Principales resultados:

  • Formación de N/B puentes de alquenilo sustituidos (5a-c) mediante un mecanismo de adición/reordenamiento por etapas.
  • Aislamiento y caracterización de un intermediario estable de aziridinio y borato de betaína.
  • Descomposición de dihidrógeno heterolítico por FLPs 5a-c en condiciones suaves para obtener productos NH+/BH- (9a-c).
  • Observación de enlaces dobles C=C con configuración Z en los productos, lo que indica el equilibrio rotacional.

Conclusiones:

  • Se han sintetizado con éxito nuevos N/B FLPs con puentes alqueniles.
  • Los FLP exhiben capacidades de activación de dihidrógeno eficientes.
  • El mecanismo de reacción implica un intermediario zwitteriónico y la apertura del anillo.