Journal
TETRAHEDRON LETTERS
Volume 55, Issue 34, Pages 4763-4766Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.07.002
Keywords
Tetrazines; Norbornenes; Click chemistry; Kinetics; Inverse electron demand Diels-Alder reactions
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Funding
- Austrian Science Fund (FWF) [T 578-N19]
- Austrian Science Fund (FWF) [T578] Funding Source: Austrian Science Fund (FWF)
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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 norbomene-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 norbomene whereas (+/-)-endo, exo-dimethy1-5-norbomene-2,3-dicarboxylate reacted only insignificanty faster than unstrained alkenes. (C) 2014 The Authors. Published by Elsevier Ltd.
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