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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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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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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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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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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Catalytic Environmentally Friendly Protocol for Achmatowicz Rearrangement.

Zhilong Li1, Rongbiao Tong1

  • 1Department of Chemistry, The Hong Kong University of Science and Technology , Clearwater Bay, Kowloon, Hong Kong, China.

The Journal of Organic Chemistry
|May 12, 2016
PubMed
Summary

A new catalytic Achmatowicz rearrangement (AchR) method using Oxone/KBr offers an eco-friendly alternative to traditional oxidants. This greener approach yields highly functionalized dihydropyranones with simplified purification due to minimal byproducts.

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Area of Science:

  • Organic Synthesis
  • Green Chemistry

Background:

  • The Achmatowicz rearrangement (AchR) is a key reaction in organic synthesis.
  • Conventional AchR methods often employ oxidants like m-CPBA and NBS, generating stoichiometric organic waste.
  • There is a need for more sustainable and environmentally friendly protocols for AchR.

Purpose of the Study:

  • To develop a novel catalytic and greener protocol for the Achmatowicz rearrangement.
  • To identify a catalytic system that minimizes or eliminates organic side products.
  • To facilitate the purification process and improve overall efficiency.

Main Methods:

  • Mechanism-guided analysis was employed to design the new protocol.
  • A catalytic system utilizing Oxone and potassium bromide (KBr) was developed.
  • The protocol was tested for its efficiency in achieving the Achmatowicz rearrangement.

Main Results:

  • The new Oxone/KBr catalytic method achieved the Achmatowicz rearrangement in excellent yields.
  • Potassium sulfate (K2SO4) was identified as the sole inorganic side product, simplifying purification.
  • The protocol was successfully integrated with subsequent transformations.

Conclusions:

  • A highly efficient and environmentally friendly catalytic method for Achmatowicz rearrangement has been established.
  • This greener protocol significantly reduces waste and simplifies product isolation.
  • The method enables rapid access to valuable highly functionalized dihydropyranones.