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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.4K
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.
7.4K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
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 reactions,...
2.2K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.5K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.2K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
7.2K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.7K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.7K
Preparation of Epoxides03:00

Preparation of Epoxides

9.0K
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 acids to...
9.0K

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Related Experiment Video

Updated: Jan 10, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Iron-mediated C(sp3) transthioetherification.

Yuanjie Yang1, Mingzhe Zhang1, Elias Picazo1

  • 1Department of Chemistry, Loker Hydrocarbon Research Institute, University of Southern California, 837 Bloom Walk, Los Angeles, California 90089-1661, United States.

Tetrahedron
|November 27, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a new iron-mediated method for transthioetherification, enabling the exchange of sulfur groups in C(sp3) benzylic thioethers. This advancement expands the utility of thioether chemistry for synthesizing valuable compounds.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Area of Science:

  • Organic Chemistry
  • Sulfur Chemistry
  • Catalysis

Background:

  • Thioethers and disulfides are crucial sulfur-containing functional groups in various applications, including pharmaceuticals, agrochemicals, and materials science.
  • Transthioetherification offers a facile route for sulfur group exchange, but existing methods are restricted to sp2-hybridized thioethers.
  • Developing methods for C(sp3) thioether functionalization is essential for expanding synthetic capabilities.

Purpose of the Study:

  • To report a novel method for C(sp3) transthioetherification of benzylic thioethers.
  • To demonstrate the utility of iron catalysis for this transformation.
  • To explore reaction conditions and substrate scope for practical applications.

Main Methods:

  • Iron-mediated C(sp3) transthioetherification of benzylic thioethers using disulfide reagents.
  • Optimization of reaction conditions, including the use of substoichiometric benzylic bromide and lower temperatures.
  • Evaluation of substrate scope with diverse functional groups on both coupling partners.

Main Results:

  • Successful development of an iron-catalyzed transthioetherification for benzylic thioethers.
  • The reaction proceeds efficiently under mild conditions, facilitated by substoichiometric benzylic bromide.
  • The method is tolerant of various functional groups, allowing for broad applicability in synthesizing complex molecules.

Conclusions:

  • This study presents a significant advancement in sulfur chemistry by enabling C(sp3) transthioetherification.
  • The iron-mediated protocol offers a versatile and practical approach for synthesizing thioether-containing compounds.
  • The ability to influence product concentration with disulfide loading provides an additional handle for synthetic control.