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Intramolecular Hydrogen Transfer During Oxidation of β-Hydroxysulfides and α-(Methyl)Thioacetamide. Pulse Radiolysis and Flash Photolysis Studies

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Hydroxysulfuranyl radicals formed during the 'OH-induced oxidation of β-hydroxy-sulfides and α-(methyl)thioacetamide immediately fragmented to yield alkylthiomethyl radicals and, as stable products, formaldehyde or carbon dioxide, respectively. No intermediary sulfur radical cations and their dimeric three-electron bonded complexes (S...S)+ were observed at neutral to alkaline pH in contrast to when the sulfur radical cations were generated at low pH or through the 4-carboxybenzophenone-sensitized photooxidation. A detailed mechanism, including a hydrogen transfer between the hydroxy/amide group and the oxygen of the hydroxysulfuranyl moiety, within a six-membered cyclic structure, is proposed and discussed.

Affiliations: 1: Institute of Nuclear Chemistry and Technology, 03-195 Warsaw, Poland; 2: Radiation Laboratory, University of Notre Dame, IN 46556, USA; 3: Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznan, Poland; 4: Department of Pharmaceutical Chemistry, University of Kansas, KS 66047, USA


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