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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Scalable Syntheses of Graphene Oxide and Reduced Graphene Oxide using Cascade Design Oxidation and Highly Basic Reduction Reactions
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Sulfur-functionalized graphene oxide by epoxide ring-opening.

Helen R Thomas1, Alexander J Marsden, Marc Walker

  • 1Department of Chemistry, University of Warwick, Coventry, CV4 7AL (UK).

Angewandte Chemie (International Ed. in English)
|June 5, 2014
PubMed
Summary
This summary is machine-generated.

Researchers developed thiol-functionalized graphene oxide (GO-SH) from graphene oxide (GO) and butyl bromide (GO-SBu). GO-SBu exhibits improved thermal stability and selectively binds gold nanoparticles, showing potential for advanced material applications.

Keywords:
epoxide openinggold nanoparticlesgraphenegraphene oxidethiols

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Area of Science:

  • Materials Science
  • Nanotechnology
  • Chemical Synthesis

Background:

  • Graphene oxide (GO) is a versatile material with potential applications in various fields.
  • Functionalization of GO is crucial for tailoring its properties and expanding its utility.
  • Developing novel GO derivatives with enhanced stability and specific binding capabilities is an active area of research.

Purpose of the Study:

  • To synthesize and characterize a novel thiol-functionalized graphene oxide material.
  • To investigate the thermal stability of the synthesized materials.
  • To explore the potential of the functionalized GO for binding noble metals, specifically gold.

Main Methods:

  • Graphene oxide (GO) was treated with potassium thioacetate, leading to ring-opening of epoxide groups and formation of thiol-functionalized GO (GO-SH).
  • Further reaction of GO-SH with butyl bromide yielded butyl-functionalized GO (GO-SBu).
  • Thermal stability was assessed, and the affinity for gold was demonstrated through nanoparticle deposition experiments.

Main Results:

  • A new thiol-functionalized graphene oxide (GO-SH) was successfully synthesized.
  • The butyl-functionalized GO (GO-SBu) exhibited significantly enhanced thermal stability compared to GO and GO-SH.
  • GO-SH demonstrated a high affinity for gold, enabling the selective deposition of a high density of gold nanoparticles.

Conclusions:

  • The developed method provides a facile route to thiol-functionalized graphene oxide.
  • The enhanced thermal stability of GO-SBu makes it suitable for applications requiring robust materials.
  • The selective gold-binding capability of GO-SH opens avenues for its use in sensing, catalysis, and nanotechnology.