Abstract
The photodecomposition of triphenylsulfonium hexafluoroantimonate was studied by pseudo-steady-state and time-resolved CIDNP experiments, using naphthalene and 9,10-dimethylanthracene as (singlet) sensitizers. Key intermediates of these reactions are radical pairs consisting of the sensitizer radical cation Sens•+ and the phenyl radical Ph•, which are formed by photoinduced electron transfer followed by cleavage of the resulting neutral onium radical. The chemical fate of Ph• is strongly influenced by the sensitizer. With 9,10-dimethylanthracene, in-cage hydrogen abstraction from the methyl groups of Sens•+ produces benzene and a carbocation that can function as a protic acid; free radicals Ph• attack surplus sensitizer to give addition products. With naphthalene, geminate combination of the two radicals and in-cage oxidation of diphenyl sulfide (the by-product of cleavage of the onium radical) by Sens•+ are observed. In both systems, the solvent scavenges free Ph•, yielding monodeuteriobenzene. The rate ...
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