102244-56-4Relevant academic research and scientific papers
Mechanistic organic chemistry in a microreactor. Zeolite-controlled photooxidations of organic sulfides
Clennan, Edward L.,Zhou, Wenhui,Chan, Jacqueline
, p. 9368 - 9378 (2007/10/03)
The intrazeolite and solution photooxygenations of a series of sulfides have been compared. The unusual zeolite environment enhances the rates of reaction, it suppresses the Pummerer rearrangements, and it has a dramatic effect on the sulfoxide/sulfone ratio. A detailed kinetic study utilizing trapping experiments and intramolecular competition provides evidence for cation complexation to a persulfoxide intermediate as the underlying phenomenon for the unique intrazeolite behavior. For example, the enhanced rate of reaction is traced to the cation stabilization of the persulfoxide toward unproductive decomposition to substrate and triplet oxygen.
PHOTOSENSITIZED OXYGENATION OF CYCLIC SULFIDES. SELECTIVE C-S BOND CLEAVAGE
Takata, Toshikazu,Ishibashi, Koichi,Ando, Wataru
, p. 4609 - 4612 (2007/10/02)
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.
