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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.
4.8K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.1K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.1K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

6.1K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
6.1K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.2K
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.
6.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

2.2K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping.

Nico Seling1, Masakazu Atobe1,2, Kevin Kasten1

  • 1Department of Chemistry, University of York, York, YO10 5DD, UK.

Angewandte Chemie (International Ed. in English)
|November 20, 2023
PubMed
Summary

Researchers developed a new method for synthesizing α-substituted cyclic sulfides. This straightforward lithiation-trapping procedure creates over 50 diverse compounds, offering a valuable tool for organic synthesis.

Keywords:
Cyclic SulfidesOrganolithiumα-Functionalization

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry
  • Synthetic Methodology

Background:

  • Cyclic sulfides are important structural motifs in various chemical compounds.
  • Existing methods for synthesizing α-substituted cyclic sulfides are limited in scope and efficiency.

Purpose of the Study:

  • To develop a general and straightforward procedure for the synthesis of α-substituted saturated sulfur heterocycles.
  • To expand the accessibility of diverse cyclic sulfide derivatives through a novel synthetic route.

Main Methods:

  • The study employed a lithiation-trapping strategy.
  • Cyclic sulfides, including tetrahydrothiophene, tetrahydrothiopyran, and thiomorpholine, were subjected to lithiation.
  • The resulting lithiated intermediates were trapped with a wide array of electrophiles.

Main Results:

  • A general and straightforward procedure for lithiation-trapping of cyclic sulfides was successfully established.
  • Over 50 diverse α-substituted saturated sulfur heterocycles were synthesized.
  • The methodology demonstrated broad applicability with various electrophiles.

Conclusions:

  • The developed methodology provides efficient access to α-substituted cyclic sulfides.
  • This new synthetic route overcomes limitations of current methods for preparing these valuable heterocyclic compounds.