Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

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...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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.

You might also read

Related Articles

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

Sort by

Same author

Speciation, Complexation of Antimonite, and Its pH Dependence in Aqueous Solution: Insights from First-Principles Molecular Dynamics Simulations.

Inorganic chemistry·2026

Same author

Adsorption of Molybdenum on Goethite Surface: A First-Principles Molecular Dynamics Simulation.

Inorganic chemistry·2026

Same author

Acupoint Application for Constipation in Thoracolumbar Compression Fracture.

Journal of visualized experiments : JoVE·2026

Same author

An Exclusive Synthesis of Macrocyclic Trimer over Polymers.

Organic letters·2026

Same author

Cyclicurilarenes: Hybridizing Bambusurils with Macrocyclic Arenes.

Organic letters·2026

Same author

An accurate and efficient framework for modeling multimetal competitive adsorption on clay minerals.

Proceedings of the National Academy of Sciences of the United States of America·2026

Same journal

An intrinsically stretchable nanowire-based sensing patch for wearable analysis of sweat chloride ion composition.

Chemical communications (Cambridge, England)·2026

Same journal

A sterically rigid-flexible balanced NHC-Pd precatalyst for room-temperature solvent-free C-N coupling of benzocyclic amines.

Chemical communications (Cambridge, England)·2026

Same journal

Portable fluorescent conjugated microporous polymer sensor coupled with a smartphone for on-site Fe<sup>3+</sup> detection in water.

Chemical communications (Cambridge, England)·2026

Same journal

Accelerated discovery of NO<sub>3</sub>RR single-atom catalysts <i>via</i> high-throughput DFT and machine learning.

Chemical communications (Cambridge, England)·2026

Same journal

Wafer-scale robust graphene electronics under industrial processing conditions.

Chemical communications (Cambridge, England)·2026

Same journal

Subnanoscale IrW oxide anodes: breaking immiscibility for high activity and durability in water electrolysis.

Chemical communications (Cambridge, England)·2026

See all related articles

Search research articles

Related Experiment Video

Updated: Jun 3, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Tröger's base-embedded macrocycles with chirality.

Conghao Shi¹, Guangzhou Xu¹, Heng Qiu¹

¹State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China. jjl@nju.edu.cn.

Chemical Communications (Cambridge, England)

|January 9, 2025

Summary

This summary is machine-generated.

This review highlights Tröger

More Related Videos

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Related Experiment Videos

Last Updated: Jun 3, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Macrocycles are essential in supramolecular chemistry.
Tröger's base (TB) offers rigidity and chirality for novel macrocycle construction.
Synthesizing TB-embedded macrocycles is challenging due to structural strain.

Purpose of the Study:

To review existing research on Tröger's base (TB)-embedded macrocycles.
To explore the linkers and structure-property relationships in these macrocycles.
To guide future synthesis of advanced TB-containing macrocycles.

Main Methods:

Literature review of TB-embedded macrocycles.
Analysis of synthetic challenges and linker strategies.
Correlation of TB properties with macrocycle characteristics.

Main Results:

Current synthesis often sacrifices TB functionality to achieve macrocyclization.
The full potential of TB in macrocycles remains underexplored.
Understanding linker influence is crucial for successful synthesis.

Conclusions:

Further research is needed to overcome synthetic hurdles in TB-macrocycle construction.
Optimizing linker design can better utilize TB's inherent properties.
This review provides a foundation for developing superior TB-embedded macrocycles.