Photosensitized electron transfer oxidation of sulfides: structure and medium effect

Oxidation of a series of sulfides R'SR (R', dodecyl, phenethyl, benzyl, cumyl, benzhydryl; R, ethyl, phenyl) under photoinduced electron transfer conditions (sensitizers: 9,10-dicyanoanthracene, triphenylpyrylium tetrafluoroborate) yields sulfoxides, products of trapping of the alkyl cation (for the benzhydryl and cumyl derivatives), and mainly aldehydes or ketones that result from alpha-deprotonation. The competing paths from the sulfide radical cation are discussed in this paper.