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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Limitations of Friedel–Crafts Reactions01:26

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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

2.1K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Phase II Conjugation Reactions: Overview01:14

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Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
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Phase II Reactions: Miscellaneous Conjugation Reactions01:19

Phase II Reactions: Miscellaneous Conjugation Reactions

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Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...
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Related Experiment Video

Updated: May 2, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Recent developments in asymmetric phase-transfer reactions.

Seiji Shirakawa1, Keiji Maruoka

  • 1Laboratory of Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

Angewandte Chemie (International Ed. in English)
|March 2, 2013
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Summary
This summary is machine-generated.

Chiral phase-transfer catalysis offers a green and efficient approach to organic synthesis. This method enables simple, mild, and scalable production of valuable compounds, advancing sustainable chemistry.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Catalysis

Background:

  • Phase-transfer catalysis (PTC) is a versatile synthetic method.
  • PTC offers operational simplicity, mild conditions, and scalability.
  • It aligns with green chemistry principles for sustainable synthesis.

Purpose of the Study:

  • To highlight the significance of chiral phase-transfer catalysis.
  • To showcase its role in developing practical and sustainable organic synthesis protocols.
  • To review advancements in asymmetric transformations using chiral PTC.

Main Methods:

  • Utilizing chiral onium salts and crown ethers as catalysts.
  • Employing phase-transfer catalysis for asymmetric synthesis.
  • Developing practical and scalable protocols for organic reactions.

Main Results:

  • Established numerous asymmetric transformations.
  • Facilitated the synthesis of valuable organic compounds.
  • Demonstrated the environmental benefits of PTC systems.

Conclusions:

  • Chiral phase-transfer catalysis is a powerful tool for green organic synthesis.
  • The field has seen significant advancements in recent years.
  • PTC provides efficient and sustainable routes to complex molecules.