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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems01:15

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Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
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Redox Titration: Other Oxidizing and Reducing Agents

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Besides iodine, other oxidizing or reducing agents can serve as titrants in redox titrations. Common oxidizing titrants include KMnO4, cerium(IV), and K2Cr2O7. The choice of oxidizing titrants depends on factors like stability, cost, analyte strength, and reaction rate between the analyte and titrant. KMnO4 is a strong oxidizing titrant that reduces from Mn(VII) to Mn(II) in a highly acidic solution, simultaneously oxidizing the analyte to a higher oxidation state. In this case, KMnO4 acts as a...
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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Preparation and Reactions of Thiols

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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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Updated: May 24, 2025

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A Completely Metal-Free Protocol for Oxidative Desulfitative C-N Coupling Reaction in Non-Basic Condition.

Partha Das1, Souvik Mondal1, Subhajit Goswami1

  • 1Department of Chemistry, Presidency University, 86/1 College Street, Kolkata, 700073, India.

Chemistry, an Asian Journal
|March 5, 2025
PubMed
Summary

This study introduces a metal-free C-N coupling reaction using hypervalent iodine to activate thiols in rhodanine derivatives. This efficient method avoids harsh conditions and is environmentally friendly, producing solid sulfur instead of toxic hydrogen sulfide.

Keywords:
2-amino-5-alkylidene-thiazol-4-onesC−N Couplingdesulfitativehypervalent iodinemetal free

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Area of Science:

  • Organic Chemistry
  • Sustainable Chemistry

Background:

  • Metal-catalyzed C-N coupling reactions often require harsh conditions like high temperatures, inert atmospheres, and strong bases.
  • Developing metal-free alternatives is crucial for sustainable chemical synthesis.

Purpose of the Study:

  • To report a novel metal-free oxidative desulfitative C-N coupling reaction.
  • To utilize a latent thiol functionality in rhodanine derivatives for C-N bond formation.
  • To achieve efficient coupling with poorly nucleophilic aromatic amines under mild conditions.

Main Methods:

  • Activation of the latent thiol group in 5-alkylidene-rhodanine using a hypervalent iodine reagent.
  • Employing ethanol as an eco-friendly solvent.
  • Conducting the reaction at 50°C under ambient atmosphere.

Main Results:

  • Successful C-N coupling between rhodanine derivatives and various amines, including poorly nucleophilic aromatic amines.
  • The reaction proceeds efficiently without metal catalysts, inert atmosphere, high temperatures, or strong bases.
  • Solid sulfur is precipitated as a byproduct, avoiding the release of hazardous hydrogen sulfide (H₂S).

Conclusions:

  • This protocol offers a novel, efficient, and environmentally benign method for C-N coupling.
  • The reaction's mild conditions and avoidance of toxic byproducts make it highly suitable for sustainable synthesis.
  • This approach provides a valuable alternative to traditional metal-catalyzed C-N coupling methods.