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Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Updated: Jun 5, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

2,3,4-Tribromo-thio-phene.

Tony M Kuriger¹, Stephen C Moratti, Jim Simpson

¹Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details the crystal structure of a brominated organic sulfur compound. Molecules form chains via hydrogen bonds and sheets through weak bromine interactions, revealing its solid-state arrangement.

Area of Science:

Crystallography
Solid-state chemistry
Organic chemistry

Background:

Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
Halogenated organic molecules exhibit diverse intermolecular interactions that dictate crystal packing.
Sulfur-containing organic compounds present unique bonding characteristics.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(4)HBr(3)S.
To identify and analyze the intermolecular interactions governing the crystal packing.
To describe the resulting supramolecular architecture in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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Analysis of bond lengths, bond angles, and intermolecular distances was performed.

Hydrogen bond analysis and halogen bonding interactions were investigated.

Main Results:

The asymmetric unit contains two essentially planar molecules of C(4)HBr(3)S.
Bifurcated C-H⋯Br hydrogen bonds link molecules into one-dimensional chains.
Weak Br⋯Br interactions (3.634–3.691 Å) further assemble these chains into undulating sheets within the bc plane.

Conclusions:

The crystal structure of C(4)HBr(3)S is characterized by a combination of C-H⋯Br hydrogen bonds and Br⋯Br interactions.
These interactions lead to a layered supramolecular arrangement, forming undulating sheets.
The findings provide insight into the structure-property relationships of halogenated organic sulfur compounds.