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Related Concept Videos

Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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.
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...
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

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Published on: January 19, 2016

Trifluoromethyl nitrones: from fluoral to optically active hydroxylamines.

Thierry Milcent1, Nathan Hinks, Danièle Bonnet-Delpon

  • 1Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Univ. Paris-Sud, rue J.B. Clément, 92296 Châtenay-Malabry, France.

Organic & Biomolecular Chemistry
|May 12, 2010
PubMed
Summary

Researchers synthesized trifluoromethyl nitrones and trifluoroethyl hydroxylamines using readily available starting materials. This study demonstrates a new method for creating valuable fluorinated compounds with high optical purity.

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Synthetic Methodology

Background:

  • Trifluoromethyl groups are crucial in pharmaceuticals and agrochemicals.
  • Efficient synthesis of trifluoromethylated compounds remains a challenge.

Purpose of the Study:

  • To develop a high-yield synthesis of trifluoromethyl nitrones.
  • To achieve diastereoselective synthesis of optically active trifluoroethyl hydroxylamines.

Main Methods:

  • Condensation of hydroxylamines with trifluoroacetaldehyde hydrate to form nitrones.
  • Nucleophilic addition of organometallic reagents to the synthesized nitrones.

Main Results:

  • Trifluoromethyl nitrones were obtained in high yields.
  • Optically active trifluoroethyl hydroxylamines were synthesized with good yields and high diastereoselectivity.

Conclusions:

  • A robust method for synthesizing trifluoromethyl nitrones was established.
  • The developed method provides access to valuable chiral trifluoroethyl hydroxylamines.