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 Experiment Videos

Diazocinones: synthesis and conformational analysis.

Lori I Robins1, Richard D Carpenter, James C Fettinger

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

The Journal of Organic Chemistry
|March 11, 2006
PubMed
Summary

Researchers synthesized conformationally restricted 1,2,4,5-tetrazines and studied their eight-membered heterocycles. Two distinct, non-interconverting conformations were identified, with kinetic and thermodynamic data providing insights into their stability and conversion.

Related Concept Videos

You might also read

Related Articles

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

Sort by
Same author

Ligand Redox Reactivity Supports C-F Activation at Al(III).

Inorganic chemistry·2026
Same author

Synthesis and biological evaluation of novel β-keto ether-triazole hybrids as dual antimicrobial and anticancer agents.

BMC chemistry·2026
Same author

A Hydroxy-Substituted Trialkyloxonium Ion and Its Oxonium Alkoxide Zwitterion.

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

Enantioselective Synthesis of Complex Carbocycles by C-H Insertion of Aryl/Aryl Carbenes.

ACS catalysis·2026
Same author

Coamorphous Solid Dispersion of a Soluble Epoxide Hydrolase Inhibitor t-TUCB with Amino Acid l-Arginine.

Organic process research & development·2026
Same author

Remote Stereocontrol in Aryl/Alkyl C-H Insertion Reactions of Rhodium Carbenes: Assembly of Pseudorigidols A and B.

Organic letters·2026

Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry
  • Physical Organic Chemistry

Background:

  • 1,2,4,5-Tetrazines are versatile building blocks in organic synthesis.
  • Cyclobutanone derivatives offer unique structural constraints for creating novel heterocyclic systems.
  • Understanding conformational dynamics is crucial for predicting chemical reactivity and biological activity.

Purpose of the Study:

  • To synthesize novel conformationally restricted 6,7-dihydro-5H-[1,2]diazocin-4-ones.
  • To investigate the conformational behavior of these eight-membered heterocycles using spectroscopic and computational methods.
  • To determine the kinetics and thermodynamics of conformational interconversion.

Main Methods:

  • Condensation reaction between 1,2,4,5-tetrazines and isoxazolylcyclobutanones.

Related Experiment Videos

  • Solution-state 1H Nuclear Magnetic Resonance (NMR) spectroscopy at variable temperatures.
  • Kinetic analysis of conformational exchange.
  • Electronic structure calculations.
  • X-ray crystallographic analysis.

    • Main Results:

    • Synthesis of conformationally restricted 6-isoxazol-5-yl-6,7-dihydro-5H-[1,2]diazocin-4-ones.
    • Identification of two non-interconverting conformations in solution at ambient temperature.
    • Determination of an activation energy of approximately 21 kcal/mol for the conformational conversion.
    • An equilibrated ratio of approximately 5:1 for thermodynamic to kinetic conformers was observed.
    • Computational predictions of geometries agreed with experimental crystallographic data for the thermodynamic conformer.

    Conclusions:

    • The synthesized dihydrodiazocinones exhibit significant conformational restriction.
    • Variable temperature NMR spectroscopy effectively probes the dynamic conformational landscape.
    • The study provides valuable insights into the stability and interconversion pathways of eight-membered heterocyclic systems.
    • Computational and experimental data corroborate the conformational assignments.