publication . Other literature type . Article . 2012

2-Hydroxyphenacyl ester: a new photoremovable protecting group

Bokolombe Pitchou Ngoy; Peter Šebej; Tomáš Šolomek; Bum Hee Lim; Tomáš Pastierik; Bong Ser Park; Richard S. Givens; Dominik Heger; Petr Klán;
  • Published: 06 Jul 2012
  • Publisher: Royal Society of Chemistry (RSC)
Abstract
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.
Subjects
free text keywords: Article, Physical and Theoretical Chemistry, Leaving group, Protecting group, Chemistry, Photodissociation, Photochemistry, Flash photolysis, Ion, Organic chemistry, Moiety, Enol, chemistry.chemical_compound, Triplet state
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publication . Other literature type . Article . 2012

2-Hydroxyphenacyl ester: a new photoremovable protecting group

Bokolombe Pitchou Ngoy; Peter Šebej; Tomáš Šolomek; Bum Hee Lim; Tomáš Pastierik; Bong Ser Park; Richard S. Givens; Dominik Heger; Petr Klán;