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.
Related projects:	Proteins in metabolism and interaction of organisms with the environment Design and Applications of Photoremovable Protecting Groups