Issue 11, 2002
From the journal:

Photochemical & Photobiological Sciences

2,5-Dimethylphenacyl esters: A photoremovable protecting group for phosphates and sulfonic acids†

Petr Klán,*a   Anna Paola Pelliccioli,*b   Tomáš Pospíšila  and  Jakob Wirz*b  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, CZ - 611 37 Brno, Czech Republic
E-mail: klan@sci.muni.cz
Fax: +420-5-41129641
Tel: +420-5-41211214

b Departement Chemie der Universität Basel, Klingelbergstrasse 80, CH-4056 Basel, Switzerland
E-mail: J.Wirz@unibas.ch
Fax: +41-61-2673855
Tel: +41-61-2673842

Abstract

2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields Φ = 0.71 and 0.68 in methanol, 0.09 and 0.19 in benzene. In methanol solution the reactions proceed predominantly via the (Z)-photoenol, the lifetimes of which (20 and 25 µs) were determined by laser flash photolysis. The chromophore is proposed as an excellent photoremovable protecting group for use in organic synthesis and biochemistry.

Graphical abstract: 2,5-Dimethylphenacyl esters: A photoremovable protecting group for phosphates and sulfonic acids

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Article information

DOI
https://doi.org/10.1039/B208171G
Article type
Paper
Submitted
21 Aug 2002
Accepted
24 Sep 2002
First published
18 Oct 2002

Photochem. Photobiol. Sci., 2002,1, 920-923

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2,5-Dimethylphenacyl esters: A photoremovable protecting group for phosphates and sulfonic acids

P. Klán, A. Paola Pelliccioli, T. Pospíšil and J. Wirz, Photochem. Photobiol. Sci., 2002, 1, 920 DOI: 10.1039/B208171G

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