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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

Preparation of Nitriles

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 1° Amines: Hofmann and Curtius Rearrangement Overview

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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.

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Related Experiment Video

Updated: Jun 1, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

N-(2-Bromo-phen-yl)thio-urea.

Halima F Saleem¹, Bohari M Yamin

¹School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a bromo-benzene thio-urea compound. Intermolecular hydrogen bonds stabilize the structure, forming linear chains.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular interactions is key in chemical physics.
Crystal structure analysis provides insights into intermolecular forces.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(7)H(7)BrN(2)S.
To investigate the intermolecular interactions and their role in crystal stabilization.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and intermolecular contacts.

Main Results:

The thio-urea unit and bromo-benzene fragment exhibit a dihedral angle of 80.82(16)°.
N-H⋯S intermolecular hydrogen bonds were identified as the primary stabilizing force.
These hydrogen bonds organize the molecules into linear chains along the ab diagonal.

Conclusions:

The crystal packing is dominated by specific intermolecular hydrogen bonding.
The observed geometry influences the overall crystal lattice stability.