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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

4.4K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
4.4K
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
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.0K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Preparation, Characterization, and Mechanistic Considerations for 1,1,1-Tri(thioacetyl)ethane and

Erik S Goebel1, Matthew J Turcotte1, Madeleine J Henley1

  • 1Department of Chemistry, University of Minnesota, 207 Pleasant Avenue SE, Minneapolis, Minnesota 55455, United States.

The Journal of Organic Chemistry
|May 3, 2023
PubMed
Summary

Researchers synthesized two novel thioacetyl compounds, 1,1,1-tri(thioacetyl)ethane and 1,1-di(thioacetyl)ethene. Mechanistic studies revealed new synthetic routes and potential applications for these versatile chemical compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Acetyl methoxy(thiocarbonyl) sulfide and potassium methyl xanthate are key reagents in sulfur chemistry.
  • The synthesis of novel organosulfur compounds is crucial for developing new materials and pharmaceuticals.

Purpose of the Study:

  • To synthesize and characterize two new thioacetyl compounds: 1,1,1-tri(thioacetyl)ethane and 1,1-di(thioacetyl)ethene.
  • To elucidate the reaction mechanisms involved in their formation.
  • To explore the synthetic utility of these novel compounds through further transformations.

Main Methods:

  • Reaction of acetyl methoxy(thiocarbonyl) sulfide with potassium methyl xanthate.
  • Mechanistic studies including reaction pathway analysis.
  • Further chemical transformations of the synthesized compounds.

Main Results:

  • Successful synthesis of 1,1,1-tri(thioacetyl)ethane and 1,1-di(thioacetyl)ethene.
  • Elucidation of reaction mechanisms leading to these compounds.
  • Demonstration of several chemical transformations of the new compounds.

Conclusions:

  • The study successfully synthesized two new thioacetyl compounds.
  • Understanding the reaction mechanisms enabled the development of streamlined synthetic routes.
  • The demonstrated transformations highlight the potential synthetic utility of these novel compounds in organic chemistry.