2,5-Dimethylphenacyl carbonates: a photoremovable protecting group for alcohols and phenols
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
15616690
DOI
10.1039/b408851d
Knihovny.cz E-resources
- MeSH
- Alcohols chemistry MeSH
- Benzene Derivatives chemical synthesis chemistry MeSH
- Phenols chemistry MeSH
- Photochemistry MeSH
- Photolysis MeSH
- Quantum Theory MeSH
- Lasers MeSH
- Molecular Structure MeSH
- Carbonates chemical synthesis chemistry MeSH
- Ultraviolet Rays MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alcohols MeSH
- Benzene Derivatives MeSH
- Phenols MeSH
- Carbonates MeSH
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.
References provided by Crossref.org
Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials
Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy
The power of solvent in altering the course of photorearrangements
