C−O Bond Fragmentation of 4-Picolyl- and <i>N</i>-Methyl-4-picolinium Esters Triggered by Photochemical Electron Transfer

Abstract

Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.