Kinetic Studies of Inverse Electron Demand Diels-Alder Reactions (iEDDA) of Norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2014 Aug 26

PMID 25152544

Citations 23

Authors

Astrid-Caroline Knall

Manuel Hollauf

Christian Slugovc

Affiliations

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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, ,-5-norbornene-2,3-dimethanol was found to be almost as reactive as unsubstituted norbornene whereas (±)-,-dimethyl-5-norbornene-2,3-dicarboxylate reacted only insignificanty faster than unstrained alkenes.

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