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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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

Diazonium Group Substitution: –OH and –H

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

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

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.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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First reductive dimerization of a polycyclic azine.

Jean-Claude Berthet1, Pierre Thuéry, Cécile Baudin

  • 1CEA, IRAMIS, SIS2M, CNRS URA 331, 91191 Gif-sur-Yvette, France. jean-claude.berthet@cea.fr

Dalton Transactions (Cambridge, England : 2003)
|September 18, 2009
PubMed
Summary

Potassium reduces the tptz molecule to an anion-radical. Samarium and Uranium reductively couple tptz into a bis-triazinide ligand, forming dinuclear complexes where metal ions bind to the ligand.

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Area of Science:

  • Coordination Chemistry
  • Organometallic Chemistry
  • Inorganic Chemistry

Background:

  • The tptz molecule is a versatile ligand in coordination chemistry.
  • Reductive coupling reactions are crucial for synthesizing complex ligands and metal complexes.

Purpose of the Study:

  • To investigate the reduction and coupling of the tptz molecule using different reducing agents.
  • To synthesize and characterize novel dinuclear samarium and uranium complexes featuring the bis-triazinide ligand.

Main Methods:

  • Reduction of tptz with potassium.
  • Reductive coupling of tptz with SmI(2) and UI(3)(py)(4).
  • Synthesis and characterization of dinuclear samarium and uranium complexes.

Main Results:

  • Potassium reduces tptz to its anion-radical in K(tptz)(2).
  • SmI(2) and UI(3)(py)(4) reductively couple tptz into a bis-triazinide ligand.
  • Novel dinuclear samarium and uranium complexes with the [tptz-tptz](2-) ligand were synthesized.

Conclusions:

  • The tptz molecule exhibits diverse reactivity towards different reducing agents.
  • The bis-triazinide ligand, formed via reductive coupling, can effectively chelate metal ions in dinuclear complexes.