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Paper | Regular issue | Vol 60, No. 12, 2003, pp.2653-2668
Published online, 2nd October, 2003
DOI: 10.3987/COM-03-9875
Selective Nucleophilic Substitutions on Tetrazines

Zoltán Novák, Beatrix Bostai, Márton Csékei, Krisztián Lörincz, and András Kotschy*

*Department of General and Inorganic Chemistry, Eötvös Loránd University, Pázmány Péter s. 1/A, H-1117 Budapest, Hungary

Abstract

A series of tetrazine derivatives bearing a leaving group were reacted with different nucleophiles to undergo either the expected substitution reaction or an unexpected exchange of the other substituent of the tetrazine ring selectively. The influence of the choice of nucleophile as well as the substituents on the tetrazine was examined in detail and the interpretation of the results was also supported by quantum chemical calculations.