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Journal Articles Organic & Biomolecular Chemistry Year : 2017

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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Dates and versions

hal-01513562 , version 1 (25-04-2017)

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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 & Biomolecular Chemistry, 2017, 15 (16), pp.3435 - 3443. ⟨10.1039/C7OB00121E⟩. ⟨hal-01513562⟩
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