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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.3K
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 and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.9K
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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.9K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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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

4.3K
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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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.2K
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).
2.2K

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Related Experiment Video

Updated: Jul 19, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

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A Thiol-Michael Approach Towards Versatile Functionalized Cyclic Titanium-Oxo Clusters.

Xing-Han Li1,2, Shuqi Dai1, Xiao-Yun Yan3

  • 1South China Advanced Institute for Soft Matter Science and Technology, School of Emergent Soft Matter, South China University of Technology, Guangzhou, 510640, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 16, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a new thiol-Michael addition method for modifying cyclic titanium-oxo clusters (CTOCs). This efficient technique enables versatile functionalization of transition metal clusters for advanced material applications.

Keywords:
functionalizationhybrid materialsnanoatomsthiol-Michael reactionstitanium-oxo clusters

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Area of Science:

  • Materials Science
  • Inorganic Chemistry
  • Supramolecular Chemistry

Background:

  • Designing novel giant molecules is crucial for advancing superlattice engineering.
  • Inorganic transition metal clusters offer potential as building blocks for new materials.
  • Efficiently functionalizing precise transition metal clusters presents a significant challenge.

Purpose of the Study:

  • To develop an efficient method for the chemical modification of cyclic titanium-oxo clusters (CTOCs).
  • To establish a versatile platform for the functionalization of precise transition metal clusters.

Main Methods:

  • Utilized a thiol-Michael addition reaction for the modification of CTOCs.
  • Investigated reaction efficiency, conditions, completeness of addition, and functional group tolerance.

Main Results:

  • Demonstrated a highly efficient thiol-Michael addition approach for CTOC modification.
  • Achieved high yields of fully functionalized CTOCs.
  • The method exhibits mild reaction conditions, high atom economy, and broad functional group tolerance.

Conclusions:

  • The developed thiol-Michael addition approach provides an effective strategy for versatile functionalization of CTOCs.
  • This method facilitates the creation of precisely functionalized transition metal clusters for diverse applications in materials science.