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Related Concept Videos

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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.
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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.
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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.
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme activation, sulfur...
Sulfur Assimilation01:20

Sulfur Assimilation

Sulfur is an essential element in biological systems, contributing to synthesizing key biomolecules, including amino acids such as cysteine and methionine, and cofactors such as coenzyme A and biotin. Microorganisms primarily assimilate sulfur as sulfate (SO₄²⁻) from the environment, which must undergo a series of biochemical transformations before it can be incorporated into cellular components. As sulfate is highly oxidized, it must undergo assimilatory sulfate reduction to become...

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Related Experiment Video

Updated: Jun 21, 2026

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
09:16

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Published on: May 20, 2019

Sulfenylation Chemistry using Polymer-Supported Sulfides.

David C Forbes1, Sampada V Bettigeri, Nahla N Al-Azzeh

  • 1Department of Chemistry, University of South Alabama, Mobile, AL 36688, USA.

Tetrahedron Letters
|August 6, 2009
PubMed
Summary

This study introduces a novel sulfenylation method using phenyl succinimidyl sulfide for activated methylenes. The process allows for selective oxidation and fragmentation, yielding valuable organic compounds and demonstrating polymer-supported sulfides as effective sulfenylating agents.

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Last Updated: Jun 21, 2026

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
09:16

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

Published on: May 20, 2019

Synthesis of Ligand-free CdS Nanoparticles within a Sulfur Copolymer Matrix
09:15

Synthesis of Ligand-free CdS Nanoparticles within a Sulfur Copolymer Matrix

Published on: May 1, 2016

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Sulfenylation Reactions

Background:

  • Sulfenylation reactions are crucial for introducing sulfur functionalities into organic molecules.
  • Activated methylenes are versatile building blocks in organic synthesis.
  • Development of efficient and selective sulfenylation methods remains an active area of research.

Purpose of the Study:

  • To develop a clean and efficient method for the sulfenylation of activated methylenes.
  • To explore the selective oxidation and thermal fragmentation of sulfenylated products.
  • To demonstrate the utility of polymer-supported sulfides as sulfenylating agents.

Main Methods:

  • Reaction of activated methylenes with phenyl succinimidyl sulfide.
  • Selective oxidation of the sulfenylated intermediate.
  • Thermal fragmentation of the oxidized product.
  • Application of a polymer-supported thioanisole derivative (JandaJel).

Main Results:

  • Clean sulfenylation of activated methylenes was achieved.
  • Selective oxidation and thermal fragmentation yielded phenylsulfenic acid and diethyl benzylidenemalonate from diethyl benzylmalonate.
  • Proof of principle for polymer-supported sulfides as effective sulfenylating agents was established through the formation of an enedicarboxylate.

Conclusions:

  • A novel and effective method for sulfenylation of activated methylenes has been developed.
  • The method allows for controlled generation of sulfenic acids and related compounds.
  • Polymer-supported sulfides offer a promising platform for solid-phase sulfenylation strategies.