2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Carboxylic Acids

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F01%3A00004579" target="_blank" >RIV/00216224:14310/01:00004579 - isvavai.cz</a>
Result on the web
—
DOI - Digital Object Identifier
—

Result language
angličtina
Original language name
2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Carboxylic Acids
Original language description
Irradiation of 2,5-dimethylphenacyl (DMP) esters (1a) in benzene or cyclohexane solutions produces the corresponding free carboxylic acids (2a) in high chemical yields, along with 6-methyl-1-indanone (3). In methanol, 2-(methoxymethyl)-5-methylacetophenone (4) is formed as a co-product. Quantum yields for the photorelease of the DMP group are higher in non-polar solvents, fi = 0.2, than in methanol, fi = 0.1. The photoreaction is initiated by efficient photoenolization, fi = 1. Three transient intermediates were identified by laser flash photolysis of 1a, the triplet state photoenol and the two ground state photoenols of Z and E configuration. Release of the acids 2a occurs predominantly from the E isomer, which has a lifetime of about 2 ms in methanoland 0.5 s in benzene solution. The present data are essential for potential applications of the DMP moiety as a photoremovable protecting group in organic synthesis or biochemistry ("caged compounds").
Czech name
—
Czech description
—

Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Publication year
2001
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)