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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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.
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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Updated: Jun 1, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
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2,5-Dichloro-thio-phene 1,1-dioxide.

Jonathan B Briggs1, Wenling Jia, Mikaël D Jazdzyk

  • 1Department of Chemistry and Materials Science Program, University of New Hampshire, Durham, NH 03824-3598, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a dichlorinated organic sulfur compound, C4H2Cl2O2S. Molecules self-assemble via hydrogen bonds, forming a symmetrical crystal lattice.

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Understanding molecular interactions in the solid state is crucial for materials science.
  • Crystal structure determination provides insights into intermolecular forces.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C4H2Cl2O2S.
  • To investigate the intermolecular interactions governing crystal packing.

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 title compound, C4H2Cl2O2S, forms a crystal structure generated by crystallographic twofold symmetry.
  • The sulfur atom is located on the rotation axis.
  • Molecules are interconnected through C-H⋯O hydrogen bonds, forming a stable crystal lattice.

Conclusions:

  • The crystal packing of C4H2Cl2O2S is primarily dictated by C-H⋯O hydrogen bonding.
  • The observed symmetry influences the overall supramolecular architecture in the solid state.