title: Kinetic studies of inverse electron demand Diels-Alder reactions (iEDDA) of norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine.
abstract: 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.
authors.affiliation: Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Astrid-Caroline
authors.initials: AC
authors.lastname: Knall
authors.affiliation: Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Manuel
authors.initials: M
authors.lastname: Hollauf
authors.affiliation: Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Christian
authors.initials: C
authors.lastname: Slugovc
keywords: Click chemistry; Inverse electron demand Diels–Alder reactions; Kinetics; Norbornenes; Tetrazines