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

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journal contribution
posted on 20.08.2004, 00:00 by Chitra Sundararajan, Daniel E. Falvey
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.