2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Phosphates and Sulfonic Acids

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Authors	KLÁN Petr PELLICCIOLI Anna Paola POSPÍŠIL Tomáš WIRZ Jakob
Year of publication	2002
Type	Article in Periodical
Magazine / Source	Photochemical and Photobiological Sciences
MU Faculty or unit	Faculty of Science
Citation
Field	Organic chemistry
Keywords	photoremovable protecting groups; photochemistry
Description	2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields F = 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 microseconds) were determined by laser flash photolysis. The chromophore is proposed as an excellent photoremovable protecting group for use in organic synthesis and biochemistry.
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