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

Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

3.6K
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...
3.6K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.3K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
11.3K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

15.9K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
15.9K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.1K
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.0K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.0K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.4K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.4K

You might also read

Related Articles

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

Sort by
Same author

Cyclobenzoin Macrocycles: Guest Capture and Applications in Energy Technologies.

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

Peristaltic Motion in Structurally Adaptive Molecular Crystals Enables Selective Propyne Capture.

Journal of the American Chemical Society·2025
Same author

Inverted azolophanes: alternant <i>o</i>-heteroarene/<i>p</i>-arene macrocycles.

Chemical science·2025
Same author

Porous Organic Polymers Incorporating Shape-Persistent Cyclobenzoin Macrocycles for Organic Solvent Separation.

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

Cycloglycolurils: Hybrid Glycoluril-Cyclobenzil Macrocycles.

Organic letters·2024
Same author

Cyclotetrabenzil Derivatives for Electrochemical Lithium-Ion Storage.

Angewandte Chemie (International ed. in English)·2023
Same journal

Electrochemical Dearomative <i>ipso</i>-Cyclization of Indolyl-ynones: A Direct Access to Trifluoromethyl/Selenyl-Spirooxindoles.

Organic letters·2026
Same journal

Photoinduced Radical Epoxidation of <i>N</i>-Alkoxyphthalimides with Allylic Peroxides.

Organic letters·2026
Same journal

B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Ring-Opening Reaction of Bicyclo[1.1.0]butanes with Silyl Ketene Imines.

Organic letters·2026
Same journal

<i>N</i>-Sulfonylaminophthalimide-Catalyzed Aerobic Oxidative Cleavage of α-C(sp<sup>3</sup>)-H and β,γ-C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Bonds of Tertiary Amines.

Organic letters·2026
Same journal

<i>O</i>-Alkylisourea-Enabled Nickel/Photoredox-Catalyzed Giese Reaction.

Organic letters·2026
Same journal

Direct Assembly of Angular 5-5-5 Tricyclic Skeletons via a Rh(III)-Catalyzed C-H Activation/Annulation Cascade.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Dec 15, 2025

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

8.3K

Three-Way Chemoselectivity Switching through Coupled Equilibria.

Thamon Puangsamlee1, Ognjen Š Miljanić1

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5003, United States.

Organic Letters
|July 15, 2020
PubMed
Summary
This summary is machine-generated.

Controlling imine oxidation selectivity in complex mixtures is difficult. Dynamic combinatorial libraries and controlled oxidant addition enable isolation of three distinct products.

More Related Videos

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.9K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.6K

Related Experiment Videos

Last Updated: Dec 15, 2025

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

8.3K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.9K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.6K

Area of Science:

  • Organic Chemistry
  • Chemical Synthesis
  • Reaction Mechanisms

Background:

  • Chemoselectivity in complex mixtures, such as biological or petrochemical feedstocks, presents significant challenges.
  • Controlling reactions in environments mimicking the primordial soup requires sophisticated strategies.
  • Imine oxidation is a key transformation but often lacks selectivity in mixed systems.

Purpose of the Study:

  • To develop a method for controlling the chemoselectivity of imine oxidation in complex chemical mixtures.
  • To investigate the use of dynamic combinatorial libraries (DCLs) for reaction control.
  • To demonstrate the isolation of specific oxidation products through precise reaction management.

Main Methods:

  • Utilized dynamic combinatorial libraries (DCLs) based on coupled imine exchange and diaza-Cope rearrangement equilibria.
  • Systematically adjusted the rate of oxidant addition to the DCL.
  • Analyzed the reaction mixture to identify and quantify dominant products.

Main Results:

  • Achieved controlled chemoselectivity in imine oxidation within a dynamic system.
  • Demonstrated that coupled equilibria in DCLs regulate the availability of oxidizable imine precursors.
  • Successfully isolated three dominant oxidation products by modulating oxidant addition rates.

Conclusions:

  • Dynamic combinatorial libraries offer a powerful platform for controlling chemoselectivity in complex reaction systems.
  • The interplay between imine exchange and diaza-Cope rearrangement is crucial for precursor availability.
  • Precise control over reaction kinetics, specifically oxidant addition rate, allows for targeted product isolation.