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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
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.6K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.6K
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
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

47.5K
sp3d and sp3d 2 Hybridization
47.5K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

1.6K
Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
1.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.6K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.6K

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Related Experiment Video

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Isothioureas as Coupling Partners in P-S Bond Formation through Cross-Dehydrogenative Coupling.

Eimear Courtney1, Gian L Reber1, Nikita Liasiuk1

  • 1School of Chemistry and Analytical and Biological Chemistry Research Facility (ABCRF), University College Cork, Cork T12 YN60, Ireland.

Organic Letters
|December 19, 2025
PubMed
Summary

Isothioureas serve as effective sulfur donors for creating phosphorus-sulfur bonds in a single step. This new method offers a simple, air-tolerant route to valuable organophosphorus compounds without harsh reagents.

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

  • Organic Chemistry
  • Organophosphorus Chemistry

Background:

  • Phosphorus-sulfur (P-S) bonds are crucial in various chemical applications.
  • Existing methods for P-S bond formation often involve harsh conditions or malodorous reagents.

Purpose of the Study:

  • To develop a mild, efficient, and operationally simple method for synthesizing P-S-containing organophosphorus compounds.
  • To utilize isothioureas as practical sulfur donors in a one-pot reaction.

Main Methods:

  • Isothioureas were used as sulfur donors.
  • Thiolate generation via piperidine treatment followed by aerobic oxidation to disulfides.
  • Cross-dehydrogenative coupling of disulfides with phosphine oxides.

Main Results:

  • High yields of phosphinothioates and related compounds were achieved.
  • The reaction proceeds efficiently under air.
  • The method tolerates a wide range of organophosphorus functional groups.
  • Avoidance of malodorous reagents and external oxidants.

Conclusions:

  • Isothioureas provide a practical and mild approach for P-S bond formation.
  • This method represents an efficient and operationally simple route to organophosphorus compounds containing P-S bonds.