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Issue 1, 2005
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2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols

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Abstract

Synthesis and photochemistry of a photochemically removable protecting group for alcohols and phenols, based on the 2,5-dimethylphenacyl (DMP) chromophore, is described. DMP carbonates release the corresponding hydroxy group containing molecules in high isolated yields (>70%), with quantum yields Φ = 0.1–0.2 in methanol and Φ = 0.36–0.51 in cyclohexane. The reactions proceed predominantly by the triplet pathway via E-photoenols, the lifetimes of which of approximately 2 s or 3 ms in cyclohexane or methanol, respectively, were determined by laser flash photolysis.

Graphical abstract: 2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols

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Article information


Submitted
11 Jun 2004
Accepted
17 Aug 2004
First published
20 Sep 2004

Photochem. Photobiol. Sci., 2005,4, 43-46
Article type
Paper

2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols

J. Literák, J. Wirz and P. Klán, Photochem. Photobiol. Sci., 2005, 4, 43
DOI: 10.1039/B408851D

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