Publication details
2-Hydroxyphenacyl ester: a new photoremovable protecting group
| Authors | |
|---|---|
| Year of publication | 2012 |
| Type | Article in Periodical |
| Magazine / Source | Photochemical & Photobiological Sciences |
| MU Faculty or unit | |
| 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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