2-Hydroxyphenacyl ester: a new photoremovable protecting group
| Autor: | Bokolombe Pitchou Ngoy, Tomáš Šolomek, Richard S. Givens, Bum Hee Lim, Tomáš Pastierik, Petr Klán, Peter Šebej, Dominik Heger, Bong Ser Park |
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| Rok vydání: | 2012 |
| Předmět: |
Anions
Photolysis 010405 organic chemistry Chemistry Lasers Photodissociation Leaving group Carbonates Acetophenones Esters 010402 general chemistry Photochemistry 01 natural sciences Enol Article 0104 chemical sciences Ion chemistry.chemical_compound Flash photolysis Moiety Quantum Theory Physical and Theoretical Chemistry Triplet state Sulfonic Acids Protecting group |
| Zdroj: | Photochemicalphotobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 11(9) |
| ISSN: | 1474-9092 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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