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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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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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[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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Preparation of Diols and Pinacol Rearrangement01:57

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Acid-Catalyzed Ring-Opening of Epoxides02:24

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.1K
Base-Catalyzed Ring-Opening of Epoxides02:26

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10.3K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.3K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.7K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
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Related Experiment Video

Updated: Feb 16, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mild, calcium catalysed Beckmann rearrangements.

H J Kiely-Collins1, I Sechi, P E Brennan

  • 1Structural Genomics Consortium & Target Discovery Institute, University of Oxford, NDM Research Building, Roosevelt Drive, Oxford, OX3 7FZ, UK. P.brennan@sgc.ox.ac.uk.

Chemical Communications (Cambridge, England)
|January 5, 2018
PubMed
Summary
This summary is machine-generated.

A novel calcium catalyst enables a mild Beckmann rearrangement, avoiding harsh conditions. This method is compatible with diverse functional groups crucial for drug discovery and natural product synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • The Beckmann rearrangement traditionally requires harsh reaction conditions.
  • These conditions limit substrate scope and functional group tolerance.
  • Developing milder alternatives is essential for complex molecule synthesis.

Purpose of the Study:

  • To develop a mild calcium-catalyzed Beckmann rearrangement.
  • To assess catalyst tolerance towards functional groups relevant in medicinal chemistry and natural product synthesis.
  • To investigate the synthetic utility and mechanism of the new reaction.

Main Methods:

  • Utilized a calcium-based catalyst system for the Beckmann rearrangement.
  • Tested catalyst compatibility with various functional groups.
  • Performed preliminary mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Successfully achieved a mild Beckmann rearrangement using calcium catalysis.
  • Demonstrated broad functional group tolerance, including groups relevant to natural products and medicinal chemistry.
  • Investigated the synthetic utility and proposed a reaction mechanism.

Conclusions:

  • A mild and functional-group-tolerant calcium-catalyzed Beckmann rearrangement has been established.
  • This method offers a valuable alternative to traditional harsh conditions for synthesizing complex molecules.
  • Further mechanistic studies provide insight into the reaction's operation.