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Related Concept Videos

Preparation of Nitriles01:12

Preparation of Nitriles

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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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 mixture.
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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Structural Isomerism02:34

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can be...

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Published on: September 8, 2013

Recent advances in isocyanide insertion chemistry.

Guanyinsheng Qiu1, Qiuping Ding, Jie Wu

  • 1Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.

Chemical Society Reviews
|March 5, 2013
PubMed
Summary

Isocyanide insertion chemistry is crucial for C1 building blocks. This review highlights recent advancements in Lewis/Brønsted acid and transition-metal-catalyzed isocyanide insertions into various bonds.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Isocyanides are versatile C1 synthons with diverse reactivity.
  • Established reactions like Passerini and Ugi highlight isocyanide utility.
  • Ongoing research seeks efficient isocyanide insertion methodologies.

Purpose of the Study:

  • To review recent progress in isocyanide insertion chemistry.
  • To categorize advancements based on catalytic systems: acid-catalyzed and transition-metal-enabled.
  • To summarize insertions into key bond types: heteroatom-hydrogen, carbon-halogen, carbon-hydrogen, and metal carbenes.

Main Methods:

  • Literature review focusing on isocyanide insertion reactions.
  • Categorization of reactions based on Lewis/Brønsted acid catalysis.
  • Categorization of reactions based on transition-metal catalysis.

Main Results:

  • Detailed summary of Lewis/Brønsted acid-catalyzed isocyanide insertions.
  • Comprehensive overview of transition-metal-enabled isocyanide insertions.
  • Specific examples of isocyanide insertion into heteroatom-hydrogen, carbon-halogen, carbon-hydrogen bonds, and metal carbenes are presented.

Conclusions:

  • Significant advancements have been made in isocyanide insertion chemistry.
  • Both acid and transition-metal catalysis offer powerful routes for isocyanide functionalization.
  • This review provides a valuable resource for understanding current isocyanide insertion methodologies.