Kinetic studies of inverse electron demand Diels-Alder reactions (iEDDA) of norbornenes and dipyridin-2-yl-1,2,4,5-tetrazine

Astrid-Caroline Knall*, Manuel Hollauf, Christian Slugovc

*Corresponding author for this work

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Inverse electron demand Diels–Alder additions (iEDDA) between 1,2,4,5-tetrazines and olefins have recently found widespread application as a novel ‘click chemistry’ scheme and as a mild technique for the modification of materials. Norbornenes are, due to their straightforward synthetic availability, especially interesting in the latter context. Therefore, the reactivity of different norbornene-based compounds was compared with unsubstituted norbornene and other alkenes using UV-vis measurements for the determination of reaction rates under pseudo first order conditions. Thereby, exo,exo-5-norbornene-2,3-dimethanol was found to be almost as reactive as unsubstituted norbornene whereas (±)-endo,exo-dimethyl-5-norbornene-2,3-dicarboxylate reacted only insignificanty faster than unstrained alkenes.
Original languageEnglish
Pages (from-to)4763-4766
JournalTetrahedron Letters
Issue number34
Publication statusPublished - 2014

Treatment code (Nähere Zuordnung)

  • Basic - Fundamental (Grundlagenforschung)

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