Use of furoin as probe molecule for the involvement of singlet oxygen in aqueous phase photoinduced transformations

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Abstract
The reactivity of furoin with various photogenerated reactive species has been studied. The oxidation of furoin by hydroxyl radicals, produced by photolysis of dilute hydrogen peroxide solutions at 253.7 nm, leads to 5‐hydroxyfuranone, furaldehyde and furoic acid. It was found k5 = 1.3 × 1010 M−1.s−1. The oxygenation of furoin by singlet oxygen, obtained by rose bengal photosensitization, gives rise to 5‐hydroxyfuranone and 1‐furanyl‐2‐dihydroxyethanone with k2 = 1.8 × 108 M−1.s−1. Superoxide anion generated by photolysis of concentrated hydrogen peroxide solutions and RO2 obtained by photolysis of 4,4'‐azobis‐4 cyanovaleric acid in the presence of oxygen reacts with furoin with a very low rate constant. Thus, furoin can be used as a test molecule for hydroxyl radicals and singlet oxygen involvements in aqueous phase photoinduced transformations.