AI Article Synopsis
- Researchers explored the use of p-hydroxyphenacyl (pHP) as a photoremovable protecting group (PPG) for both simple and complex phenolic compounds, including tyrosine.
- The study revealed that the ability of phenols to leave as Brønsted groups influences the reaction outcomes, leading to varied byproducts based on the acidity of the phenolic compounds.
- In specific conditions, such as using octa acid containers, unexpected byproducts were generated, deviating from typical reactions like the Favorskii rearrangement.
Article Abstract
Extending the applications of Photoremovable Protecting Groups (PPGs) to "cage" phenols has generally met with unusually complex PPG byproducts. In this study, we demonstrate that the p-hydroxyphenacyl (pHP) cage for both simple and complex phenolics, including tyrosine, dispenses free phenols. With the simpler unsubstituted phenols, the reaction is governed by their Brønsted Leaving Group ability. On the other hand, the byproducts of the cage vary with these phenols. For the more acidic phenols the cage byproduct follows the Favorskii rearrangement to form p-hydroxyphenylacetic acid whereas for the weaker phenols other reactions such as reduction and hydrolysis begin to emerge. When the photolysis is conducted in octa acid (OA) containers, non-Favorskii, unrearranged fragments of the cage and other byproducts arise.
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| http://dx.doi.org/10.1039/d0pp00067a | DOI Listing |
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