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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.5K
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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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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
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.7K
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.
5.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.5K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.5K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

3.0K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
3.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.6K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Updated: Jan 19, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols.

John M Lopp1, Valerie A Schmidt1

  • 1Department of Chemistry and Biochemistry , University of California San Diego , 9500 Gilman Drive , La Jolla , California 92093 , United States.

Organic Letters
|September 26, 2019
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Summary
This summary is machine-generated.

This study introduces a novel sulfur atom transfer process enabling thiols to generate carbon-centered radicals. This method facilitates reductive coupling with diverse alkenes, offering a new synthetic pathway.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Thiols are versatile functional groups in organic synthesis.
  • Generating carbon-centered radicals from thiols is synthetically valuable.
  • Existing methods for thiol-based radical generation have limitations.

Purpose of the Study:

  • To develop a new method for generating carbon-centered radicals from thiols.
  • To establish a reductive coupling process utilizing these radicals.
  • To explore the scope and limitations of the developed methodology.

Main Methods:

  • A sulfur atom transfer process was developed using triethyl phosphite as the sulfur atom acceptor.
  • Thiols were used as precursors for carbon-centered radicals.
  • Reductive coupling reactions with various alkenes were performed.

Main Results:

  • The developed process successfully generates carbon-centered radicals from thiols.
  • A wide range of functionalized and electronically unbiased alkenes participate in the reductive coupling.
  • The reaction proceeds via the exchange of weak S-H and C-S bonds for C-H, C-C, and S-P bonds.

Conclusions:

  • A novel and efficient method for thiol-derived radical generation and subsequent reductive coupling has been established.
  • This methodology offers a versatile approach for synthesizing complex molecules.
  • The process is driven by favorable bond energy exchanges, highlighting its mechanistic basis.