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Related Concept Videos

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 Alkynes: Alkylation Reaction02:27

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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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Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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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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Step-Growth Polymerization: Overview01:03

Step-Growth Polymerization: Overview

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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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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Related Experiment Video

Updated: Feb 20, 2026

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
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Tailored Modification of Thioacrylates in a Versatile, Sequence-Defined Procedure.

Joshua O Holloway1, Suzan Aksakal2, Filip E Du Prez1

  • 1Polymer Chemistry Research Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Science, Ghent University, Krijgslaan 281 S4-bis, Ghent, B-9000, Belgium.

Macromolecular Rapid Communications
|October 26, 2017
PubMed
Summary

This study introduces a novel method for creating sequence-defined oligomers. The iterative synthesis uses selective side-group insertion and thiophenol-catalyzed amidation for precise control over oligomer structure.

Keywords:
amidationsequence-defined polymersthioacrylatethiolactone

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Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Synthetic Chemistry

Background:

  • Controlled synthesis of sequence-defined oligomers is crucial for developing advanced materials.
  • Existing methods often lack efficiency or versatility in sequence control.

Purpose of the Study:

  • To develop a novel, iterative strategy for synthesizing sequence-defined oligomers.
  • To enable precise control over oligomer sequence and structure variation.

Main Methods:

  • A thiolactone-based, multistep iterative protocol was designed.
  • Thioacrylates were utilized in combination with solid-phase synthesis for step-by-step oligomer growth.
  • Selective side-group insertion via thiophenol-catalyzed amidation reactions was employed.

Main Results:

  • The protocol successfully generated sequence-defined oligomers.
  • Sequence definition and structure variation were achieved by substituting thioacrylate side groups with diverse amines.
  • Liquid chromatography-mass spectrometry and high-resolution mass spectroscopy confirmed conversion and purity.

Conclusions:

  • The developed strategy provides an effective approach for synthesizing sequence-defined oligomers.
  • This method offers a versatile platform for creating oligomers with tailored sequences and structures.
  • The findings advance the field of precise macromolecular synthesis.