Abstract
We report the clean, efficient photorelease of a series of carboxylic acids embedded in octa acid (OA) host and protected by a p-hydroxyphenacyl cage. A key role is played by the cage by providing hydrophobicity for entry into the OA enclosure and yet readily removable as a photoactivated protecting group for release from the host. The rapid photo-Favorskii rearrangement of the departing chromophore does not react with the host OA but diminishes hydrophobicity of the OA contents, leading to their facile release into the solvent.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1276-1279 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 17 |
| Issue number | 5 |
| DOIs | |
| State | Published - Mar 6 2015 |
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
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Jagadesan, P., Da Silva, J. P., Givens, R. S., & Ramamurthy, V. (2015). Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger. Organic Letters, 17(5), 1276-1279. https://doi.org/10.1021/acs.orglett.5b00252