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Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

Authors
Jang, MiLim, Bum HeeRyu, Hyuk JunPark, Bong Ser
Issue Date
25-Dec-2013
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
Temperature effect; Photochemistry; Photoremovable protecting group; Benzocyclobutenol
Citation
TETRAHEDRON LETTERS, v.54, no.52, pp 7175 - 7179
Pages
5
Indexed
SCI
SCIE
SCOPUS
Journal Title
TETRAHEDRON LETTERS
Volume
54
Number
52
Start Page
7175
End Page
7179
URI
https://scholarworks.dongguk.edu/handle/sw.dongguk/21978
DOI
10.1016/j.tetlet.2013.10.109
ISSN
0040-4039
1873-3581
Abstract
Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of In(IN/CB) versus 1/T gave a straight line from which Ea(IN)-Ea(CB) and A(IN)/A(CB) were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest Ea(IN)-Ea(CB) and A(IN)/A(CB) among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3). (C) 2013 Elsevier Ltd. All rights reserved.
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