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Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.8K
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...
1.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
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,...
2.1K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.8K
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...
3.8K

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Copper and Silver Trispyrazolylborate-Phosphinoazide Complexes: Synthesis, Characterization, and Nitrene Generation.

Manuel R Rodríguez1, Francisco Molina1, M Mar Díaz-Requejo1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain.

Inorganic Chemistry
|January 2, 2025
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Summary

New phosphinoazide complexes containing copper and silver were synthesized. Thermal decomposition of these complexes yields cyclodiphosphazenes through a metal-mediated nitrene coupling reaction, with a proposed mechanistic pathway.

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Phosphinoazide complexes are precursors to various nitrogen-containing compounds.
  • Metal-mediated reactions offer novel synthetic pathways.
  • Cyclodiphosphazenes are an important class of phosphorus-nitrogen heterocycles.

Purpose of the Study:

  • To synthesize and characterize novel phosphinoazide complexes of copper and silver.
  • To investigate the thermal decomposition of these complexes.
  • To elucidate the mechanism of metal-mediated nitrene coupling leading to cyclodiphosphazenes.

Main Methods:

  • Synthesis of TpBr3M-L phosphinoazide complexes (M = Cu, Ag).
  • Structural characterization using X-ray diffraction and other spectroscopic techniques.
  • Thermal decomposition studies to identify products and reaction pathways.

Main Results:

  • Successful synthesis and structural confirmation of novel phosphinoazide complexes.
  • Formation of cyclodiphosphazenes upon thermal decomposition.
  • Demonstration of both stoichiometric and catalytic roles of the metal in the nitrene coupling process.

Conclusions:

  • The synthesized phosphinoazide complexes are effective precursors for cyclodiphosphazene synthesis.
  • A novel metal-mediated pathway for nitrene coupling has been identified and mechanistically proposed.
  • This transformation offers a new route to cyclodiphosphazenes with potential applications in materials science and catalysis.