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

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Authors

LITERÁK Jaromír WIRZ Jakob KLÁN Petr

Year of publication 2005
Type Article in Periodical
Magazine / Source Photochemical and Photobiological Sciences
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords photochemistry; phenacyl; protecting group
Description 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 = 0.1-0.2 in methanol and = 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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