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Related Concept Videos

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...
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 Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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 Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

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Isocyanide-based two-step three-component keteneimine formation.

Didier Coffinier1, Laurent El Kaim, Laurence Grimaud

  • 1Laboratoire Chimie et Procedes, Ecole Nationale Superieure de Techniques Avancees, 32 Bd Victor, 75739 Paris Cedex 15, France.

Organic Letters
|March 27, 2009
PubMed
Summary
This summary is machine-generated.

This study introduces a solvent-free synthesis of novel keteneimines from isocyanides and acyl chlorides. The resulting compounds can be transformed into valuable phosphorylated tetrazoles and triazoles.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Isocyanide-Nef reaction is a known method for synthesizing imidoyl chlorides.
  • Perkow-type reactions are utilized for the synthesis of various heterocyclic compounds.

Purpose of the Study:

  • To develop a novel, solvent-free synthetic route to keteneimines.
  • To explore the conversion of these keteneimines into phosphorylated tetrazoles and triazoles.

Main Methods:

  • The Isocyanide-Nef reaction between isocyanides and acyl chlorides to form imidoyl chlorides.
  • Subsequent treatment of imidoyl chlorides with trialkylphosphites in a Perkow-type reaction to yield keteneimines.
  • Conversion of keteneimines to phosphorylated tetrazoles and triazoles.

Main Results:

  • Successful synthesis of keteneimines via a one-pot, solvent-free sequence.
  • Demonstration of the facile conversion of keteneimines to phosphorylated tetrazoles and triazoles.
  • The described methodology offers an efficient pathway to complex heterocyclic structures.

Conclusions:

  • A novel and efficient solvent-free method for keteneimine synthesis has been established.
  • The developed protocol provides access to valuable phosphorylated tetrazoles and triazoles.
  • This approach offers a sustainable and streamlined route in synthetic organic chemistry.