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

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

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

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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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...
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred to as...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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.

You might also read

Related Articles

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

Sort by
Same author

Toward the Synthesis of Pestalustaine A: Structural Revision and Formation of Original Strained Tricyclic Architectures.

Angewandte Chemie (International ed. in English)·2026
Same author

Strain-Release Pentafluorosulfanylation of Carbonyl-Containing Disubstituted Bicyclobutanes: A Fortuitous Path to SF<sub>5</sub>-Containing Oxa[2.1.1]bicyclohexanes.

Angewandte Chemie (International ed. in English)·2026
Same author

Reinvestigation of the mechanism and selectivity of 1,8-cineole synthase using <i>TerDockin</i>.

Chemical science·2026
Same author

Enantioselective NP-HPLC Resolution of Usnic Acid and Isousnic Acid with Revised Absolute Configuration and NMR Assignment of Isousnic Acid.

Journal of natural products·2026
Same author

The One Ring: A Monocycle Producing Class II Diterpene Cyclase from <i>Isodon leucophyllus</i>.

Journal of the American Chemical Society·2026
Same author

Investigations toward a unified reaction pathway of thermal and TBSOTf-mediated oxidopyrylium-alkene (5 + 2) cycloadditions.

Organic & biomolecular chemistry·2026

Related Experiment Video

Updated: Jun 16, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Dissecting a dyotropic rearrangement.

Rebecca L Davis1, Dean J Tantillo

  • 1Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, USA.

The Journal of Organic Chemistry
|February 4, 2010
PubMed
Summary
This summary is machine-generated.

Density functional theory calculations reveal factors influencing nitroso acetal-to-aminal rearrangements. Both concerted and stepwise pathways are energetically feasible, affected by structural and environmental conditions.

More Related 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

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Related Experiment Videos

Last Updated: Jun 16, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

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

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Nitroso acetal-to-aminal rearrangements are important organic reactions.
  • Understanding the mechanistic pathways and influencing factors is crucial for synthetic applications.

Purpose of the Study:

  • To investigate the mechanism of nitroso acetal-to-aminal rearrangements using computational methods.
  • To identify key structural and environmental factors affecting the rearrangement process.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed.
  • Analysis of transition states and intermediates for various reaction pathways.

Main Results:

  • Structural factors like ring strain, hyperconjugation, and anomeric effects significantly impact rearrangement ease.
  • Solvation effects (specific and nonspecific) also play a crucial role.
  • Both concerted and stepwise reaction mechanisms were found to be energetically viable.

Conclusions:

  • The rearrangement mechanism is sensitive to subtle structural and environmental changes.
  • Computational modeling provides valuable insights into the reaction's complexity and potential pathways.