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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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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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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...
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Preparation and Reactions of Thiols02:33

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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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Anoxygenic photosynthesis is a phototrophic process that captures light energy to drive carbon fixation without producing molecular oxygen. Unlike oxygenic photosynthesis, which utilizes water as an electron donor and releases oxygen, anoxygenic phototrophs use alternative electron donors such as hydrogen sulfide (H₂S), elemental sulfur (S⁰), or thiosulfate (S₂O₃²⁻). This process is carried out by diverse groups of bacteria, including purple bacteria, green...
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Chemolithotrophs are microorganisms that obtain energy by oxidizing inorganic molecules such as hydrogen gas (H₂), ammonia (NH₃), reduced sulfur compounds (H₂S, S²⁻), and ferrous iron (Fe²⁺). Unlike heterotrophic organisms that rely on organic carbon, chemolithotrophs transfer electrons from these inorganic donors to the electron transport chain (ETC), generating a proton motive force (PMF) that drives ATP synthesis through oxidative phosphorylation.
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Sulfur, an important element in the chemical makeup of proteins, is recycled through the atmosphere and aquatic and terrestrial environments. Found in the atmosphere as sulfur dioxide (SO2), sulfur is released by decaying organisms, weathered rocks, geothermal vents, volcanos, and burning fossil fuels. It is deposited into the ecosystem, cycled through the biotic community, and either released back into the atmosphere as gas or deposited in marine sediment for long-term storage and eventual...
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Continuous Bioinspired Oxidation of Sulfides.

Francesca Mangiavacchi1, Letizia Crociani1, Luca Sancineto1

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Summary

This study presents a simple, efficient, and selective flow oxidation of sulfides to sulfoxides and sulfones using in situ generated perselenic acid. The method shows broad applicability for various sulfide types and enables gram-scale synthesis.

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catalysisflow chemistryhydrogen peroxideoxidationselenium dioxidesulfidesulfonesulfoxide

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Process Chemistry

Background:

  • Sulfides are versatile chemical intermediates.
  • Selective oxidation of sulfides to sulfoxides and sulfones is crucial in organic synthesis.
  • Traditional oxidation methods can lack efficiency, selectivity, or scalability.

Purpose of the Study:

  • To develop a simple, efficient, and selective method for sulfide oxidation.
  • To utilize flow chemistry for improved reaction control and safety.
  • To establish a scalable synthesis of sulfoxides and sulfones.

Main Methods:

  • In situ generation of perselenic acid catalyst from selenium (IV) oxide.
  • Utilizing diluted aqueous hydrogen peroxide as the oxidant.
  • Performing the oxidation reaction under continuous flow conditions.
  • Testing a range of aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides.

Main Results:

  • Achieved simple, efficient, and selective oxidation of sulfides to sulfoxides and sulfones.
  • Demonstrated good applicability across various sulfide substrates.
  • Successfully scaled up the synthesis of (methylsulfonyl)benzene to gram-scale.

Conclusions:

  • The developed flow oxidation method offers a practical and scalable approach for sulfide oxidation.
  • In situ generated perselenic acid is an effective catalyst for this transformation.
  • The methodology is suitable for the synthesis of valuable sulfoxide and sulfone compounds.