Jaromir Literak, Jakob Wirz and Petr Klan, "2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols", Photochem. Photobiol. Sci. 2005, 4, 43-46.


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.