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Two in one--We show here that the highly strained trans,trans-diolefin (E,E)-1,5-cyclooctadiene can perform efficiently two different click reactions at fast reaction rates. It is capable of first undergoing [3+2] cycloadditions with 1,3-dipoles at a reaction rate comparable to that of strained cyclooctynes. The resulting cycloadduct can then perform a much faster inverse-electron-demand Diels-Alder reaction with tetrazines, effectively linking an azide to a tetrazine. Thus, (E,E)-1,5-cyclooctadiene could have many applications in chemical biology and polymer chemistry. This journal is © The Royal Society of Chemistry 2011


Henning Stöckmann, André A Neves, Henry A Day, Shaun Stairs, Kevin M Brindle, Finian J Leeper. E,E)-1,5-Cyclooctadiene: a small and fast click-chemistry multitalent. Chemical communications (Cambridge, England). 2011 Jul 7;47(25):7203-5

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PMID: 21611648

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