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

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

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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
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.8K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.2K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.2K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.3K
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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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Rhodium(II)-Catalyzed Hinsberg Dearomatization Using Trimethylsilyldiazomethane.

Jason R Combs1, David S Carter1, Fengyi Gu1

  • 1Department of Chemistry, University of California, Irvine, California 92617-2025, United States.

Organic Letters
|November 3, 2023
PubMed
Summary

Rhodium(II) catalysts enable carbene transfer to thioethers, forming sulfonium ylides. This reaction efficiently creates quaternary centers in complex aromatic ring systems like indoles and naphthalenes.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Sulfonium ylides are versatile intermediates in organic synthesis.
  • Quaternary carbon centers are important structural motifs in pharmaceuticals and natural products.
  • Transition metal catalysis offers efficient routes to complex molecular architectures.

Purpose of the Study:

  • To develop a novel rhodium(II)-catalyzed carbene transfer reaction.
  • To synthesize quaternary centers within aromatic ring systems.
  • To explore the scope and limitations of this new synthetic methodology.

Main Methods:

  • Carbene transfer from trimethylsilyldiazomethane catalyzed by rhodium(II) complexes.
  • Reaction with various arylmethyl thioethers, thioesters, and thiocarbamates.
  • Utilized different rhodium(II) catalysts, including Rh₂(OAc)₄ and Rh₂(cap)₄.

Main Results:

  • Efficient generation of sulfonium ylides from thioethers.
  • Successful [2,3]-sigmatropic rearrangement to form quaternary centers.
  • The reaction is effective for naphthalene, indole, and benzofuran systems.
  • Thioesters and thiocarbamates are also viable substrates.
  • Monocyclic benzene systems were unsuccessful.

Conclusions:

  • Rhodium(II) catalysis provides a powerful method for C-C bond formation.
  • This methodology enables the synthesis of complex aromatic compounds with quaternary centers.
  • The reaction offers a new strategy for accessing valuable synthetic intermediates.