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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...
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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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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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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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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Cyclic Oxothiomolybdates: Building Blocks for Cyclodextrin-Based Open Frameworks.

Maxence Lion1, Jérôme Marrot1, William Shepard2

  • 1Institut Lavoisier de Versailles, CNRS, UVSQ, Université Paris-Saclay, 45 avenue des Etats-Unis, 78035, Versailles, France.

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|September 9, 2024
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Summary

This study introduces a novel chaotropic scaffold using molybdenum-sulfur complexes to crystallize hybrid organic-inorganic materials with cyclodextrins. Different cyclodextrins create distinct structures, advancing supramolecular design.

Keywords:
Chaotropic effectCyclodextrinHybrid frameworkPolyanionX-ray structure

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Area of Science:

  • Supramolecular Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Desolvation processes are crucial in biological self-assembly but underutilized in crystalline material design.
  • Hybrid organic-inorganic systems offer unique properties by combining diverse building blocks.

Purpose of the Study:

  • To develop a novel chaotropic scaffold for crystallizing hybrid organic-inorganic systems.
  • To investigate the role of cyclodextrins in templating these structures.
  • To explore the self-assembly behavior of molybdenum-sulfur complexes.

Main Methods:

  • Synthesis of [Mo8S8O8(OH)8(guest)]2- complexes.
  • Crystallization with alpha- and beta-cyclodextrins.
  • Characterization using X-ray diffraction (powder and single-crystal), N2 adsorption, elemental analysis, thermogravimetric analysis.
  • Solution studies including 1H NMR titration and small-angle X-ray scattering (SAXS).

Main Results:

  • Successful formation of hybrid organic-inorganic crystalline architectures using the novel scaffold.
  • Beta-cyclodextrin (β-CD) promoted host-guest complex formation.
  • Alpha-cyclodextrin (α-CD) induced a Kagome-type structure with significant voids.
  • Evidence of pre-association of building units in solution.

Conclusions:

  • The [Mo8S8O8(OH)8(guest)]2- complex serves as an effective chaotropic scaffold for supramolecular crystallization.
  • Cyclodextrins play a critical templating role, directing the formation of different structural motifs.
  • This work provides new insights into the design principles for inorganic polyanion-cyclodextrin supramolecular assemblies.