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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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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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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

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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...
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Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Thioketones as a Simple Route Toward Thioester-Based Materials.

Anne D Fernando Pulle1,2, Hendrik Frisch1,2, Bryan T Tuten3

  • 1School of Chemistry and Physics, Queensland University of Technology, 2 George Street, Brisbane, QLD, 4000, Australia.

Macromolecular Rapid Communications
|May 19, 2025
PubMed
Summary

Thioketones are now effective monomers for Passerini polymerization, creating polymers with thioester backbones. These novel polymers offer tunable properties and easy modification for advanced soft matter applications.

Keywords:
multicomponent chemistrypasserini reactionspolymer chemistrypolymeric materialsthiol chemistry

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Multicomponent polymerizations offer efficient routes to complex polymer architectures.
  • Thiocarbonyl compounds are less explored as monomers compared to their carbonyl counterparts.
  • Developing new monomers is crucial for expanding the scope of polymer synthesis and material properties.

Purpose of the Study:

  • To demonstrate the utility of thioketones as monomers in Passerini multicomponent polymerizations.
  • To synthesize polymers featuring thioester linkages in the polymer backbone.
  • To explore the tunable properties and post-polymerization modification capabilities of these novel polymers.

Main Methods:

  • Utilized thioketones as monomers in Passerini multicomponent reactions.
  • Characterized the resulting polymers using standard analytical techniques.
  • Investigated polymer degradability via aminolysis.
  • Explored dynamic trans-thioesterification for glass transition tuning.
  • Applied thiol-ene chemistry for thermoset material formation.

Main Results:

  • Successfully polymerized thioketones via Passerini multicomponent reactions.
  • Synthesized polymers containing thioester groups directly in the polymer backbone.
  • Demonstrated the ease of handling thioketone monomers compared to thioaldehydes.
  • Showcased facile tuning of material properties, including degradation, glass transition temperature, and crosslinking.

Conclusions:

  • Thioketones are effective and user-friendly monomers for Passerini polymerization.
  • The resulting thioester-containing polymers possess versatile and tunable properties.
  • These polymers represent a promising platform for developing advanced soft matter materials with tailored functionalities.