Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

10.9K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
10.9K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.3K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.3K
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

4.6K
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
4.6K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

4.2K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
4.2K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

4.0K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
4.0K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

3.7K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
3.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Ki-67 shapes the nucleolus by anchoring chromatin via its amphiphilic properties.

The EMBO journal·2026
Same author

Bis(trifluoromethyl)disulfide and the EtP<sub>4</sub> Phosphazene Base-Formation of a Bench-Stable [EtP<sub>4</sub>SCF<sub>3</sub>]<sup>+</sup>[SCF<sub>3</sub>]<sup>-</sup> Salt.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Bis(pentafluoroethyl)arsinous Acid and the Bis(pentafluoroethyl)arsinite─Synthesis, Structural Characterization and Transition-Metal Complexes.

Inorganic chemistry·2026
Same author

Tuning reactivity through implementation of the HSAB concept in oxygen- and sulphur-bridged Al/P and Ga/P FLPs.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Perfluoroalkylated Arsoranide Salts: Syntheses and Structural Insights.

Inorganic chemistry·2026
Same author

Low-Concentration Electrolytes Based on Weakly Coordinating Anions for Applications in Lithium-Ion-Batteries and Lithium-Metal-Batteries.

Angewandte Chemie (International ed. in English)·2025
Same journal

Expanding Cyanide-Bridged Weakly Coordinating Anions Through the Brominated Silver Salt Ag[BCNB<sup>Br</sup>].

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Photoexcited Nickel(0)-Catalyzed Direct Decarboxylative Cross-Coupling.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Divergent Total Syntheses of Bisnicalaterine Alkaloids Enabled by a Stereocontrolled Geissoschizol Synthesis.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Ultramicroporous Metal-Organic Frameworks Functionalized With Acyclic Ether Oxygen Bonds for Efficient C<sub>2</sub>H<sub>2</sub>/CO<sub>2</sub> and C<sub>2</sub>H<sub>2</sub>/C<sub>2</sub>H<sub>4</sub> Separation.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Metal-Support Synergy in Nitrogen-Doped Carbon-Supported Ru Nanoparticles Enables Base-Free Aerobic Oxidation of Isononanol to Isononanoic Acid.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Visible Light-Induced Alkyne-Carbonyl Metathesis in Multicomponent Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
See all related articles
  1. Home
  3. Stable Cyclic Peterson Olefination Intermediates.
  1. Home
  3. Stable Cyclic Peterson Olefination Intermediates.

Related Experiment Video

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K

Stable Cyclic Peterson Olefination Intermediates.

Julia Landwehrmann1, Beate Neumann1, Hans-Georg Stammler1

  • 1Fakultät für Chemie, Centrum für Molekulare Materialien, Universität Bielefeld, Bielefeld, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 23, 2026

View abstract on PubMed

Summary
This summary is machine-generated.

Researchers synthesized stable cyclic intermediates for the Peterson olefination, a silicon-based carbonyl olefination reaction. This study provides crucial evidence for cyclic intermediates in this important organic chemistry transformation.

Keywords:
carbanionsfluorineolefinationreactive intermediatessilicates

More Related Videos

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

10.4K
Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

10.9K

Related Experiment Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K
Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

10.4K
Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

10.9K

Area of Science:

  • Organic Chemistry
  • Organosilicon Chemistry

Background:

  • The Wittig olefination is a well-understood method for carbonyl olefination.
  • The mechanism of the related Peterson olefination, a silicon analogue, remains less understood.
  • Evidence for cyclic intermediates in Peterson olefination has been scarce.

Purpose of the Study:

  • To synthesize and characterize stable cyclic intermediates of the Peterson olefination.
  • To provide experimental evidence supporting the existence of cyclic intermediates in this reaction.

Main Methods:

  • Reaction of α-silyl carbanions with various ketones.
  • Synthesis of α-silyl carbanions stabilized by three pentafluoroethyl groups and a phenyl group.

Main Results:

  • Successful synthesis and characterization of several stable cyclic Peterson olefination intermediates.
  • Demonstration of the feasibility of forming cyclic intermediates under specific conditions.

    • Conclusions:

    • The study presents the first stable cyclic Peterson olefination intermediates.
    • This work offers significant insights into the mechanism of the Peterson olefination reaction.