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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