Publication details

2-Hydroxyphenacyl ester: a new photoremovable protecting group

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NGOY Bokolombe Pitchou ŠEBEJ Peter ŠOLOMEK Tomáš LIM Bum Hee PASTIERIK Tomáš PARK Bong Ser GIVENS Richard HEGER Dominik KLÁN Petr

Year of publication 2012
Type Article in Periodical
Magazine / Source Photochemical & Photobiological Sciences
MU Faculty or unit

Faculty of Science

Field Organic chemistry
Keywords Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group
Description 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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