title: 2-Hydroxyphenacyl ester: a new photoremovable protecting group.
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.
authors: Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.
authors: Bokolombe Pitchou
authors: BP
authors: Ngoy
authors: Peter
authors: P
authors: Sebej
authors: Tomáš
authors: T
authors: Solomek
authors: Bum Hee
authors: BH
authors: Lim
authors: Tomáš
authors: T
authors: Pastierik
authors: Bong Ser
authors: BS
authors: Park
authors: Richard S
authors: RS
authors: Givens
authors: Dominik
authors: D
authors: Heger
authors: Petr
authors: P
authors: Klán
mesh_terms: D000098:Acetophenones / Q000138:chemical synthesis / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D004952:Esters; D007834:Lasers; D010782:Photolysis; D011789:Quantum Theory; D013451:Sulfonic Acids / Q000737:chemistry
chemical_list: D000098:Acetophenones; D000838:Anions; D002254:Carbonates; D004952:Esters; D013451:Sulfonic Acids