AI Article Synopsis
- A new photoremovable protecting group for carboxylates and sulfonates is introduced, utilizing a 2-hydroxyphenacyl moiety that absorbs light below 370 nm.
- Laser flash photolysis and sensitization studies reveal that the group releases its leaving component from a brief triplet state.
- DFT-based quantum calculations indicate that a key reaction step involves triplet excited state intramolecular proton transfer, with additional pathways involving triplet anions and quinoid triplet enol intermediates also identified.
Article 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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3422872 | PMC |
| http://dx.doi.org/10.1039/c2pp25133g | DOI Listing |
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