2-Hydroxyphenacyl ester: a new photoremovable protecting group

被引：0
|
作者：
Bokolombe Pitchou Ngoy
Peter Šebej
Tomáš Šolomek
Bum Hee Lim
Tomáš Pastierik
Bong Ser Park
Richard S. Givens
Dominik Heger
Petr Klán
机构：
[1] Masaryk University,Department of Chemistry, Faculty of Science
[2] Masaryk University,Research Centre for Toxic Compounds in the Environment, Faculty of Science
[3] Dongguk University,Department of Chemistry
[4] University of Kansas,Department of Chemistry
来源：
Photochemical & Photobiological Sciences | 2012年 / 11卷
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摘要：
A 2-hydroxyphenacyl moiety absorbing below 370 nm is proposed as a new photoremovable protecting group for carboxylates and sulfonates. Laser flash photolysis and steady-state sensitization studies show that the leaving group is released from a short-lived triplet state. In addition, DFT-based quantum chemical calculations were performed to determine the key reaction steps. We found that triplet excited state intramolecular proton transfer represents a major deactivation channel. Minor productive pathways involving the triplet anion and quinoid triplet enol intermediates have also been identified.
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页码：1465 / 1475
页数：10
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