Electron transfer in the photochemistry of substituted benzoate and naphthoate esters

Abstract
Substituted alkyl esters of aromatic carboxylic acids (ArCO2CH2CH2X) undergo photochemical cleavage to give the carboxylic acid. If X is a dialkylamino- or methylthio-group, the reaction is relatively efficient (ϕ up to ca. 0.25), and this is attributed to the operation of an electron-transfer mechanism. Excited state lifetime measurements provide strong support for such a mechanism; in particular the singlet lifetime is at least six times shorter for esters containing the dialkylamino-group.

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