Abstract
The photoinduced oxidation of benzyl phenyl sulfides 1–3 has been investigated in MeCN using 9,10-dicyanoanthracene as sensitizer in the presence of O 2 . In this reaction a sulfide radical cation is formed, which undergoes one or more of the three main reaction pathways opened to these species: C S bond cleavage, C H bond cleavage and S-oxidation. The former route (leading to benzylic products) was observed with all the substrates investigated, whereas the second (leading to benzaldehydes) operates only with 1 and 2 . Formation of sulfoxides was found solely in the photooxidation of 1 . The influence of substrate structures on the relative contribution of the three pathways as well as the role of O 2 in this respect are discussed. The competition between paths a-c has been studied in the 9,10-dicyanoanthracene (DCA) sensitized oxidation of 1–3 .
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