1. 2-Hydroxyphenacyl ester: a new photoremovable protecting group.
- Author
-
Ngoy BP, Sebej P, Solomek T, Lim BH, Pastierik T, Park BS, Givens RS, Heger D, and Klán P
- Subjects
- Acetophenones chemical synthesis, Anions chemistry, Carbonates chemistry, Esters, Photolysis, Quantum Theory, Sulfonic Acids chemistry, Acetophenones chemistry, Lasers
- 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.
- Published
- 2012
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