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[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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Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.3K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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

2.7K
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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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Ph2SCCO: A New Versatile CCO-Fragment Transfer Reagent.

Qiu Sun1,2, Julian Hauda1, David Tymann1

  • 1Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Str. 6, 44227, Dortmund, Germany.

Angewandte Chemie (International Ed. in English)
|October 10, 2025
PubMed
Summary
This summary is machine-generated.

A new reagent, Ph2S═C═C═O, provides controlled reactivity for ketenylidene (C2O) in organic synthesis. This breakthrough enables practical applications for C2O synthons, leading to novel cyclopropanation and epoxidation reactions.

Keywords:
Bicyclo[3.1.0]hexanesCCO fragment transferCyclopropanationHeterocumulenesSulfur ylides

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Small Molecule Reactivity

Background:

  • Ketenylidene (C2O) is a small molecule with potential as a C2 synthon.
  • Its high reactivity limits practical applications in organic synthesis.

Purpose of the Study:

  • To develop a stable and controllable reagent for C2O transfer.
  • To explore the synthetic utility of this new reagent in organic transformations.

Main Methods:

  • Synthesis of the heterocumulene Ph2S═C═C═O (1).
  • Investigation of its reactivity profile, including reactions with Brønsted acids.
  • Exploitation of the resulting sulfur ylide intermediate for subsequent reactions.

Main Results:

  • The heterocumulene (1) acts as a well-defined C2O equivalent.
  • It exhibits integrated ketene-like and carbene reactivity.
  • Controlled CCO fragment transfer was achieved, enabling synthesis of cyclopropanation and epoxidation products.

Conclusions:

  • Ph2S═C═C═O (1) offers a practical solution for utilizing C2O reactivity in synthesis.
  • This reagent facilitates efficient access to valuable α-cyclopropyl and α-epoxy carbonyl compounds.
  • The developed strategy allows for the construction of complex bicyclic cyclopropanes.