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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Water-soluble triazabutadienes that release diazonium species upon protonation under physiologically relevant
Flora W Kimani1, John C Jewett
1Department of Chemistry and Biochemistry, University of Arizona, 1306 E University Blvd, Tucson, AZ 85721 (USA).
Abstract:
Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water-soluble. It is shown that these molecules readily release diazonium species in a pH-dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo-release strategies and organelle-specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.
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