Abstract
An intramolecular isotope effect has been measured for the reaction of singlet oxygen with 2,2,8,8-tetradeuterio-1,5-dithiacyclooctane, 4d 4 . The magnitude of the isotope effect, 1.21±0.09, provides verification of removal of an α-hydrogen during the product determining step to form a hydroperoxysulfonium ylide and ultimately the sulfoxide product. The absence of any special structural features in 4d 4 to enhance the propensity of hydrogen removal is used to suggest that the hydroperoxysulfonium ylide is a ubiquitous intermediate in the reactions of sulfides with singlet oxygen.
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