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Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
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.
3.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
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...
2.0K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.8K
Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K

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Triflamides and Triflimides: Synthesis and Applications.

Mikhail Y Moskalik1, Vera V Astakhova1

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Molecules (Basel, Switzerland)
|August 26, 2022
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Triflamides and triflimides are versatile organic compounds with high NH-acidity and unique properties. Their applications span organic synthesis, catalysis, medicine, and agriculture, making them valuable reagents.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Sulfonamides, particularly triflamides (CF3SO2NHR, TfNHR), possess unique chemical properties.
  • High NH-acidity, lipophilicity, and strong electron-withdrawing nature drive their utility.
  • Bis(trifluoromethanesulfonyl)imide (triflimide, Tf2NH) is a notable example of a strong NH-acid.

Purpose of the Study:

  • To review the synthesis and diverse applications of N-trifluoromethanesulfonyl derivatives.
  • To highlight the role of triflamides and triflimides in various chemical transformations.
  • To explore their utility across organic chemistry, medicine, biochemistry, catalysis, and agriculture.

Main Methods:

  • Literature review of triflamide and triflimide synthesis.
  • Analysis of triflamide and triflimide applications in organic reactions.
  • Examination of triflimide salts as catalysts in various reaction types.

Main Results:

  • Triflamides are effective reagents, catalysts, and additives due to their acidity and electronic properties.
  • Triflimide and its salts are potent catalysts for cycloaddition, Friedel-Crafts, condensation, and heterocyclization reactions.
  • Triflamides serve as nitrogen sources in C-amination reactions, yielding valuable synthetic intermediates and ligands.

Conclusions:

  • Triflamides and triflimides are indispensable tools in modern organic chemistry and related fields.
  • Their unique properties facilitate a wide array of synthetic transformations and applications.
  • Continued exploration of these compounds promises further advancements in synthesis and catalysis.