PHOTOSENSITIZED OXYGENATION OF CYCLIC SULFIDES. SELECTIVE C-S BOND CLEAVAGE

Article abstract of DOI:10.1016/S0040-4039(00)98765-3

TPP-Senzitized photooxidation of five-membered ring sulfides in aprotic solvent afforded C-S bond cleavage products, unlike six- and seven-membered ring sulfides which gave only S-oxidation products.The products as well as substitution and concentration effects suggest that C-S bond cleavage depends upon acidity of α-proton of persulfoxide intermediate.