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Issue 11, 2002
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2,5-Dimethylphenacyl esters: A photoremovable protecting group for phosphates and sulfonic acids

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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


Submitted
21 Aug 2002
Accepted
24 Sep 2002
First published
18 Oct 2002

Photochem. Photobiol. Sci., 2002,1, 920-923
Article type
Paper

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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