Abstract
Furil underwent an efficient photoreduction to selectively afford furoin in benzene and acetonitrile containing triethylamine. A thermodynamic analysis of the reaction suggests the operation of an electrontransfer mechanism. Small steric effects of tertiary amines used on the quantum yields for the formation of furoin was explained in terms of a loose radical ion pair formed by an electron transfer from the ground-state amine to the excited singlet-state furil. A pronounced charge transfer-type interaction between the amine radical cation and benzene molecules in the solvent cage was proposed to interpret a high reactivity of furil in the nonpolar solvent, benzene.
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