Norbornenes in Inverse Electron-Demand Diels-Alder Reactions

Significant differences in the reactivity of norbornene derivatives in the inverse electron‐demand Diels–Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum‐chemical calculations were used to...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-09, Vol.19 (40), p.13309-13312
Main Authors: Vrabel, Milan, Kölle, Patrick, Brunner, Korbinian M., Gattner, Michael J., López-Carrillo, Verónica, de Vivie-Riedle, Regina, Carell, Thomas
Format: Article
Language:English
Subjects:
Anhydrides - chemistry
Chemistry
Cycloaddition Reaction
Derivatives
Diels-Alder reactions
Electrons
Inverse
inverse electron-demand Diels-Alder reactions
Isomers
Kinetics
Mathematical analysis
Molecular Structure
Norbornanes - chemistry
norbornene
Quantum chemistry
Quantum Theory
quantum-chemical calculations
Reaction kinetics
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Summary:Significant differences in the reactivity of norbornene derivatives in the inverse electron‐demand Diels–Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum‐chemical calculations were used to rationalize and support the observed experimental data.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201301838