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Published on: April 4, 2014
2,5-Dimethylphenacyl carbonates: a photoremovable protecting group for alcohols and phenols
Jaromír Literak1, Jakob Wirz, Petr Klán
1Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, CZ-611 37 Brno, Czech Republic.
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 Phi= 0.1-0.2 in methanol and Phi= 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.
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