2-Hydroxyphenacyl ester: a new photoremovable protecting group

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Authors

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

Citation
Web http://pubs.rsc.org/en/content/articlelanding/2012/pp/c2pp25133g
Doi http://dx.doi.org/10.1039/C2PP25133G
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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