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

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...
Polymer Classification: Stereospecificity01:26

Polymer Classification: Stereospecificity

Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is stabilized by...

You might also read

Related Articles

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

Sort by
Same author

Photo-Triggered, Fast, and Fluorogenic Thiophene-Based Cycloalkynes for the Bioorthogonal Fluorescent Labeling of 1,3-Dipole-Tagged Molecules in No-Wash Conditions.

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

Cobaloxime-catalysed regiodivergent hydrogen atom transfer for alkenyl and allylic carbamoylation with branched alkenes.

Nature communications·2026
Same author

Non-Enzymatic Formation of Chaxines and Natural Steroidal Derivatives via Ergosterol Air Oxidation.

The Journal of organic chemistry·2026
Same author

Computational Insight into Free Molecular Rotors in Crystalline Solids: Inertial Rotation and Langevin Dynamics.

Journal of the American Chemical Society·2026
Same author

Computational Exploration of Molecular Solar Thermal Energy Storage via Substituted Anthracenes [4 + 4] Photodimerizations and Thermal Retro-Cycloadditions in Solution and Crystalline States.

Journal of the American Chemical Society·2026
Same author

Biocatalytic Metal Hydrogen Atom Transfer for Asymmetric Olefin-Olefin Coupling.

Journal of the American Chemical Society·2026
Same journal

Erratum for the Research Article "Assessing the health risks of rice cadmium content standards in China" by H. Chu <i>et al</i>.

Science advances·2026
Same journal

Erratum for the Research Article "Developmental regulation of Erk signaling by mitotic kinases" by F. Chen <i>et al</i>.

Science advances·2026
Same journal

Magnetically levitated metasurface enabling tangible and bidirectional human-machine interaction.

Science advances·2026
Same journal

A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane.

Science advances·2026
Same journal

Turning sound and force into light with AlN:Mn<sup>2+</sup> mechanoluminescence.

Science advances·2026
Same journal

Extreme dominance of Earth-origin heavy ions in the intense ring current near the Earth during the May 2024 super geomagnetic storm.

Science advances·2026
See all related articles

Related Experiment Video

Updated: Jun 19, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Rule-breaking in chemical synthesis.

Jordan A M Gonzalez1, Giulianna A Miseo1, K N Houk1

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA.

Science Advances
|June 17, 2026
PubMed
Summary
This summary is machine-generated.

Researchers challenged established chemical rules to discover novel synthetic chemistry. This work opens new avenues for reactions involving amides and anti-Bredt olefins.

More Related Videos

Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods
07:20

Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods

Published on: October 6, 2023

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Related Experiment Videos

Last Updated: Jun 19, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods
07:20

Discovery and Synthesis Optimization of Isoreticular Al(III) Phosphonate-Based Metal-Organic Framework Compounds Using High-Throughput Methods

Published on: October 6, 2023

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Traditional chemical principles dictate specific rules for molecular structure, bonding, and reactivity.
  • Amides and anti-Bredt olefins are classes of compounds with established reactivity patterns.

Purpose of the Study:

  • To challenge and redefine existing paradigms in chemical structure, bonding, and reactivity.
  • To explore and discover new synthetic methodologies involving amides and anti-Bredt olefins.

Main Methods:

  • Investigated the fundamental principles governing chemical structure and bonding.
  • Developed novel synthetic routes by challenging established reactivity rules.
  • Utilized computational and experimental techniques to characterize new reactions.

Main Results:

  • Discovered new synthetic chemistry by overcoming limitations imposed by traditional rules.
  • Demonstrated novel reactivity patterns for amides and anti-Bredt olefins.
  • Established a foundation for further exploration of unconventional chemical transformations.

Conclusions:

  • Challenging long-standing chemical rules is a viable strategy for discovering new synthetic chemistry.
  • The findings expand the scope of known reactions for amides and anti-Bredt olefins.
  • This research provides new tools and insights for synthetic chemists.