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Related Concept Videos

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.
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...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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.

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Related Experiment Video

Updated: Jun 18, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Highly efficient cyanoimidation of aldehydes.

Ping Yin1, Wen-Bo Ma, Yue Chen

  • 1Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry,West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, PR China.

Organic Letters
|December 1, 2009
PubMed
Summary
This summary is machine-generated.

This study presents a novel catalytic method for cyanoimidation of aldehydes using cyanamide and N-bromosuccinimide (NBS). This efficient process yields valuable N-cyanobenimidates and 1,2,4-triazole derivatives under mild conditions.

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

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Last Updated: Jun 18, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: June 21, 2017

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Developing efficient synthetic routes for nitrogen-containing heterocycles is crucial in medicinal chemistry.
  • Aldehyde functionalization remains a key area for synthetic innovation.

Purpose of the Study:

  • To develop a novel, catalyst-free method for the cyanoimidation of aldehydes.
  • To explore the synthesis of N-cyanobenimidates and their subsequent conversion to 1,2,4-triazole derivatives.

Main Methods:

  • Cyanoimidation of various aldehydes using cyanamide as the nitrogen source.
  • Oxidation achieved using N-bromosuccinimide (NBS) under mild, catalyst-free conditions.
  • One-pot reaction sequence enabling intermolecular C-N and C-O bond formation.

Main Results:

  • High yields of N-cyanobenimidate products were obtained.
  • The method demonstrated mild reaction conditions and a simple workflow.
  • Subsequent cyclization of products efficiently yielded 1,2,4-triazole derivatives.

Conclusions:

  • A new, efficient, and cost-effective method for aldehyde cyanoimidation has been established.
  • The developed protocol offers a straightforward route to valuable heterocyclic compounds.
  • The catalyst-free approach highlights the potential of NBS as a versatile oxidant in organic synthesis.