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Issue 25, 2011
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(E,E)-1,5-Cyclooctadiene: a small and fast click-chemistry multitalent

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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.

Graphical abstract: (E,E)-1,5-Cyclooctadiene: a small and fast click-chemistry multitalent

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Article information


Submitted
14 Apr 2011
Accepted
26 Apr 2011
First published
24 May 2011

Chem. Commun., 2011,47, 7203-7205
Article type
Communication

(E,E)-1,5-Cyclooctadiene: a small and fast click-chemistry multitalent

H. Stöckmann, A. A. Neves, H. A. Day, S. Stairs, K. M. Brindle and F. J. Leeper, Chem. Commun., 2011, 47, 7203
DOI: 10.1039/C1CC12161H

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