159552-18-8Relevant articles and documents
Kinetics of Intramolecular Alkyl Radical Attack on Sulfur in Disulfides and Thioesters
Beckwith, Athelstan L. J.,Duggan, Sandhya A. M.
, p. 1509 - 1518 (2007/10/02)
The 4-(alkyldithio)butyl radicals 8a and c, and the 4-(phenyldithio)butyl radical 8b, generated from the corresponding esters of N-hydroxypyridine-2(1H)-thione, undergo fast exo-cyclisation by SHi attack at sulfur.Similarly, the 5-(alkyldithio)pentyl radical 8d undergoes 1,6-ring formation.The rate constants for cyclisation were determined by photolysis of the radical precursors in the presence of appropriate thiols.Butyl and pentyl radicals bearing ω-acetylthio or ω-benzoylthio substituents also undergo ring closure but much more slowly.The kinetics of these intramolecular SH2 reactions are discussed and compared with those for the intermolecular attack of hexyl radicals on diphenyl disulfide and on dibutyl disulfide.
