Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F03%3A00008279" target="_blank" >RIV/00216224:14310/03:00008279 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters
Original language description
The study of the temperature-sensitive photochemical release of a carboxylic acid from 2,5-dimethylphenacyl ester is reported. Quantum yields of the benzoate ester degradation in benzene increased from 0.22 at room temperature to 0.28 at 50 oC whereas amore significant increase (nearly by a factor of 3) was observed in methanol and ethanol, reaching a high reaction efficiency (0.25) typically found in non-polar solvents. The reaction proceeds predominantly via the triplet pathway and the E-photoenol inthe whole temperature range in methanol solution. A higher quantum efficiency in heated methanol is explained by enhancing the E-photoenol population. This picture was partially confirmed by the quantum chemical calculations. The 2,5-dimethylphenacyl chromophore is proposed as an efficient photoremovable protecting group for carboxylic acids in solutions under conventional or microwave-assisted heating for applications in organic synthesis, such as the solid-phase synthesis.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA203%2F02%2F0879" target="_blank" >GA203/02/0879: Microwave Irradiation Effect on Photochemical Reactions</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year
2003
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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