| LITERÁK, Jaromír, Stanislav RELICH, Petr KULHÁNEK a Petr KLÁN. Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters. Molecular Diversity. Basel, Switzerland: Kluwer, 2003, roč. 7, 2-4, s. 265-271. ISSN 1381-1991. |
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@article{489943,
author = {Literák, Jaromír and Relich, Stanislav and Kulhánek, Petr and Klán, Petr},
article_location = {Basel, Switzerland},
article_number = {2-4},
keywords = {photochemistry; microwave; protecting groups},
language = {eng},
issn = {1381-1991},
journal = {Molecular Diversity},
title = {Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters},
volume = {7},
year = {2003}
}
TY - JOUR
ID - 489943
AU - Literák, Jaromír - Relich, Stanislav - Kulhánek, Petr - Klán, Petr
PY - 2003
TI - Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters
JF - Molecular Diversity
VL - 7
IS - 2-4
SP - 265
EP - 265
PB - Kluwer
SN - 13811991
KW - photochemistry
KW - microwave
KW - protecting groups
N2 - 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 a more 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 in the 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.
ER -
LITERÁK, Jaromír, Stanislav RELICH, Petr KULHÁNEK a Petr KLÁN. Temperature Dependent Photochemical Cleavage of 2,5-Dimethylphenacyl Esters. \textit{Molecular Diversity}. Basel, Switzerland: Kluwer, 2003, roč.~7, 2-4, s.~265-271. ISSN~1381-1991.
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