Issue 16, 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.

Graphical abstract: Syntheses and kinetic studies of cyclisation-based self-immolative spacers

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2017
Accepted
21 Mar 2017
First published
23 Mar 2017

Org. Biomol. Chem., 2017,15, 3435-3443

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

S. Huvelle, A. Alouane, T. Le Saux, L. Jullien and F. Schmidt, Org. Biomol. Chem., 2017, 15, 3435 DOI: 10.1039/C7OB00121E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements