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@article{372911,
author = {Zabadal, Miroslav and Pelliccioli, Anna P. and Klán, Petr and Wirz, Jakob},
article_location = {USA},
article_number = {45},
keywords = {photochemistry},
language = {eng},
issn = {1089-5639},
journal = {Journal of Physical Chemistry A},
title = {2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Carboxylic Acids},
volume = {105},
year = {2001}
}
TY - JOUR
ID - 372911
AU - Zabadal, Miroslav - Pelliccioli, Anna P. - Klán, Petr - Wirz, Jakob
PY - 2001
TI - 2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Carboxylic Acids
JF - Journal of Physical Chemistry A
VL - 105
IS - 45
SP - 10329
EP - 10329
PB - The American Chemical Society
SN - 10895639
KW - photochemistry
N2 - 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 methanol and 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").
ER -
ZABADAL, Miroslav, Anna P. PELLICCIOLI, Petr KLÁN and Jakob WIRZ. 2,5-Dimethylphenacyl Esters: A Photoremovable Protecting Group for Carboxylic Acids. \textit{Journal of Physical Chemistry A}. USA: The American Chemical Society, 2001, vol.~105, No~45, p.~10329-10333. ISSN~1089-5639.
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