Syntheses and kinetic studies of cyclisation-based self-immolative spacers

Abstract : Kinetic analysis of the disassembly of self-immolative spacers based on cyclisation processes was performed. Five compounds were synthesized belonging to two different series, and their kinetic constants were determined. Electron-donating substituents gave a slight acceleration but the main effect was steric, and the Thorpe-Ingold effect was indeed particularly effective. Comparison with the self-immolative spacers based on elimination processes showed that cyclisations gave comparable or lower rate, but the corresponding spacers are more difficult to modulate.
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Submitted on : Tuesday, November 5, 2019 - 4:18:18 PM
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Steve Huvelle, Ahmed Alouane, Thomas Le Saux, Ludovic Jullien, Frédéric Schmidt. Syntheses and kinetic studies of cyclisation-based self-immolative spacers. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (16), pp.3435-3443. ⟨10.1039/c7ob00121e⟩. ⟨hal-02349391⟩



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