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

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.4K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.2K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.2K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.4K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
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.
2.5K

You might also read

Related Articles

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

Sort by
Same author

Ni(DQ)<sub>2</sub>: A Useful Gateway to Zero-Valent Nickel Complexes.

Organometallics·2026
Same author

Utilizing Single-Crystalline Transformations for Precise Atom Placement in Multicomponent Cluster-Based Coordination Networks.

Journal of the American Chemical Society·2025
Same author

Carboranes with Exopolyhedral Boron-Tetrel Bonds.

Organometallics·2025
Same author

Vertex Engineering of the Dodecaborate-Based Broadband Membrane Carriers.

Inorganic chemistry·2025
Same author

Bidirectional Modification of a <i>Galbulimima</i> Alkaloid Identifies Selective Opioid Ligands.

ACS central science·2025
Same author

A Layered, Piedfort-Aggregated Cu(I) Isocyanide Coordination Network Derived from an Encumbering Tritopic Linker.

Inorganic chemistry·2025

Related Experiment Video

Updated: Jan 15, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

11.0K

Superelectrophilic Cyclizations Involving 2-Norbornyl Dications.

Grant P Holmin1, Milan Gembicky2, Douglas A Klumpp1

  • 1Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, United States.

The Journal of Organic Chemistry
|October 13, 2025
PubMed
Summary

Researchers synthesized anilino 2-norbornyl alcohols and reacted them in acid. This novel chemistry yielded ring-fused norbornane products efficiently, suggesting a unique dicationic intermediate.

More Related Videos

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.9K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.5K

Related Experiment Videos

Last Updated: Jan 15, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

11.0K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.9K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.5K

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Synthetic Methodology

Background:

  • Anilino alcohols are versatile synthetic intermediates.
  • Norbornane derivatives are important scaffolds in medicinal chemistry.
  • Understanding reaction mechanisms is key to developing new synthetic routes.

Purpose of the Study:

  • To explore the reactivity of anilino 2-norbornyl alcohols in acidic media.
  • To develop a novel synthetic route to ring-fused norbornane products.
  • To elucidate the reaction mechanism, including potential intermediates.

Main Methods:

  • Synthesis of various anilino 2-norbornyl alcohols.
  • Reaction of these alcohols in strongly acidic conditions.
  • Characterization of the resulting products using spectroscopic methods.
  • Mechanistic studies to propose reaction pathways.

Main Results:

  • Successful preparation of 12 different ring-fused norbornane products.
  • High yields ranging from 81% to 99% achieved for the products.
  • Evidence supporting a reaction mechanism involving a novel ammonium-carbonium dicationic intermediate.

Conclusions:

  • Anilino 2-norbornyl alcohols are effective precursors for synthesizing complex norbornane structures.
  • The proposed dicationic intermediate offers new insights into carbocation chemistry.
  • This methodology provides an efficient route to valuable ring-fused norbornane compounds.