The 2,5-dimethylphenacyl chromophore, a new photoremovable protecting group for carboxylic acids, is proposed. Direct photolysis of various 2,5-dimethylphenacyl esters in benzene or methanol at 254-366 nm leads to the formation of the corresponding carboxylic acids in almost quantitative isolated yields. The photodeprotection is based on efficient intramolecular hydrogen abstraction without the necessity of introducing a photosensitizer.

Department of Organic Chemistry Faculty of Science Masaryk University Kotlarska 2 611 37 Brno Czech Republic

References provided by Crossref.org

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy

The power of solvent in altering the course of photorearrangements

Temperature dependent photochemical cleavage of 2,5-dimethylphenacyl esters