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Preparation of Nitriles01:12

Preparation of Nitriles

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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...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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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...
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Dinitrogen Cleavage and Multicoupling with Isocyanides in a Dititanium Dihydride Framework.

Qingde Zhuo1, Jimin Yang2, Xiaoxi Zhou1

  • 1Organometallic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.

Journal of the American Chemical Society
|April 5, 2024
PubMed
Summary

This study demonstrates the first cleavage of dinitrogen (N2) and its subsequent multicoupling with isocyanides using a dititanium dihydride framework. This breakthrough enables new pathways for nitrogen functionalization and the synthesis of complex organometallic compounds.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Catalysis

Background:

  • Dinitrogen (N2) activation and functionalization are crucial but challenging due to the strong N-N triple bond.
  • Developing efficient methods for N-N bond cleavage and subsequent C-N bond formation is a significant goal in chemistry.

Purpose of the Study:

  • To report the first instance of dinitrogen (N2) cleavage and selective multicoupling with isocyanides.
  • To explore the reactivity of a dititanium dihydride complex with various isocyanides.
  • To elucidate the mechanistic pathways of these complex transformations using computational methods.

Main Methods:

  • Synthesis and characterization of dititanium dihydride complexes.
  • Reactions of dinitrogen dititanium dihydride complex with different isocyanides under varying conditions.
  • Density Functional Theory (DFT) calculations to investigate reaction mechanisms.

Main Results:

  • Achieved N2 cleavage and selective multicoupling with isocyanides, forming novel amidoamidinatoguanidinate complexes.
  • Demonstrated control over reaction pathways, leading to different product complexes based on stoichiometry and temperature.
  • Successfully performed cross-coupling reactions with diverse isocyanides, yielding products with mixed isocyanide components.

Conclusions:

  • The dititanium dihydride framework effectively cleaves N2 and facilitates multicoupling with isocyanides.
  • This work provides a new synthetic strategy for nitrogen functionalization and the construction of complex nitrogen-containing molecules.
  • DFT calculations offer detailed insights into the intricate reaction mechanisms involved.