Abstract

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Henning Stöckmann, Andre A. Neves, Henry A. Day, Shaun Stairs, Kevin M. Brindle and and F. J. Leeper, "(E,E)-1,5-cyclooctadiene: A small and fast click-chemistry multitalent" Chem. Comm., 2011, 47 (25), 7203-7205. Full Text.

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-electrondemand 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.

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