Authors:
H Stöckmann, AA Neves, HA Day, S Stairs, KM Brindle, FJ Leeper
Journal name: 
Chem Commun (Camb)
Citation info: 
47(25):7203-7205
Abstract: 
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.
DOI: 
http://doi.org/10.1039/c1cc12161h
Research group: 
Brindle Group
E-pub date: 
07 Jul 2011