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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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Publication details

The article was received on 21 Aug 2002, accepted on 24 Sep 2002 and first published on 18 Oct 2002


Article type: Paper
DOI: 10.1039/B208171G
Citation: 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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