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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.8K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.6K
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...
3.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.3K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.3K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.3K
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,...
4.3K
Preparation of Nitriles01:12

Preparation of Nitriles

2.3K
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...
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Versatile New Reagent for Nitrosation under Mild Conditions.

Jordan D Galloway1, Cristian Sarabia1, James C Fettinger2

  • 1Department of Chemistry and Chemical Biology, University of California, Merced, Merced, California 95343, United States.

Organic Letters
|April 12, 2021
PubMed
Summary

A novel chemical reagent enables efficient transnitrosation under mild conditions. This stable reagent offers high functional group tolerance, accessing challenging nitroso compounds previously unavailable.

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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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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Traditional nitrosation methods often require harsh conditions.
  • Many substrates are sensitive to oxidation or reversible transnitrosation.

Purpose of the Study:

  • To develop a new chemical reagent for mild and efficient transnitrosation.
  • To synthesize challenging nitroso compounds and their isotopologues.

Main Methods:

  • Development of a novel, air- and moisture-stable transnitrosation reagent.
  • Application of the reagent across various solvents and functional group tolerant substrates.
  • Characterization of synthesized nitroso compounds, including 15N isotopologues.
  • X-ray crystallography and computational analysis of reagent isomers.

Main Results:

  • The new reagent facilitates transnitrosation under mild experimental conditions.
  • High functional group tolerance was observed, even for sensitive substrates.
  • Several challenging nitroso compounds, including 15N isotopologues, were synthesized for the first time.
  • Two stable rotational isomers of the reagent were identified, with one isomer being catalytically active.

Conclusions:

  • A versatile and stable reagent for transnitrosation has been developed.
  • This reagent expands the scope of accessible nitroso compounds.
  • Understanding of reagent isomerism and reactivity provides insights for future reagent design.