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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.5K
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.
6.5K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
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 and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.0K
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.
5.0K
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
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

1.1K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
1.1K

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Related Experiment Video

Updated: Aug 16, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Organothianthrenium salts: synthesis and utilization.

Huan Meng1, Ming-Shang Liu1, Wei Shu1

  • 1Shenzhen Grubbs Institute, Department of Chemistry, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology Shenzhen 518055 Guangdong P. R. China shuw@sustech.edu.cn.

Chemical Science
|December 22, 2022
PubMed
Summary

Organothianthrenium salts offer a versatile thianthrenation strategy for selective C-H, C-O, and other bond functionalizations. This review covers their preparation and diverse applications in catalytic processes.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Organothianthrenium salts, featuring charged and neutral sulfur atoms, are increasingly recognized for their synthetic utility.
  • Their unique structure enables diverse chemical transformations, particularly in forging new carbon-carbon and carbon-heteroatom bonds.

Purpose of the Study:

  • To review the preparation methods for various organothianthrenium salts (aryl, alkenyl, alkyl).
  • To discuss the application of these salts in catalytic processes.
  • To highlight their synthetic potential in regioselective functionalizations.

Main Methods:

  • Summarization of established synthetic routes for organothianthrenium salts.
  • Compilation of examples showcasing thianthrenation of C-H, C-O, and other bonds.
  • Review of catalytic systems employing organothianthrenium salts.

Main Results:

  • Thianthrenation provides a predictable and regioselective method for functionalizing arenes, alkenes, alkanes, alcohols, and amines.
  • These transformations often proceed under mild conditions via diverse reaction mechanisms.
  • A range of organothianthrenium salts have been successfully prepared and utilized.

Conclusions:

  • Organothianthrenium salts are valuable precursors for diverse organic transformations.
  • The thianthrenation strategy offers an efficient route for regioselective synthesis.
  • Further exploration of their catalytic applications promises significant synthetic advancements.