2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols
- 20 September 2004
- journal article
- research article
- Published by Springer Nature
- Vol. 4 (1) , 43-46
- https://doi.org/10.1039/b408851d
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.Keywords
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