2,5-dimethylphenacyl esters: a photoremovable protecting group for phosphates and sulfonic acids
Language English Country England, Great Britain Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
12659533
DOI
10.1039/b208171g
Knihovny.cz E-resources
- MeSH
- Acetophenones chemistry MeSH
- Benzene chemistry MeSH
- Esters chemistry MeSH
- Photochemistry methods MeSH
- Photolysis MeSH
- Isomerism MeSH
- Kinetics MeSH
- Quantum Theory MeSH
- Sulfonic Acids chemistry MeSH
- Lasers MeSH
- Methanol chemistry MeSH
- Organophosphates chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Acetophenones MeSH
- Benzene MeSH
- Esters MeSH
- Sulfonic Acids MeSH
- Methanol MeSH
- Organophosphates MeSH
2,5-Dimethylphenacyl phosphoric and sulfonic esters release the corresponding acids upon irradiation in nearly quantitative isolated yields, with quantum yields phi = 0.71 and 0.68 in methanol, 0.09 and 0.19 in benzene. In methanol solution the reactions proceed predominantly via the (Z)-photoenol, the lifetimes of which (20 and 25 micros) were determined by laser flash photolysis. The chromophore is proposed as an excellent photoremovable protecting group for use in organic synthesis and biochemistry.
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
Temperature dependent photochemical cleavage of 2,5-dimethylphenacyl esters
