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Abstract
Anti-thiirane S-oxides derived from cis-2,3-epoxyhexan-1-ol are prepared to serve as transition state analogs for alkene epoxidation and singlet oxygenation. The β-hydroxyl directing effect commonly exploited in sulfide oxidations is found to be completely ineffective in directing oxidation of cis-epoxy alcohol-derived thiiranes; steric factors alone appear to determine the anti:syn selectivity. Detailed 1H NMR analysis was performed on both the stable anti- and the unstable syn-thiirane S-oxides. The thiirane S-oxide ring protons are found to possess unusually large vicinal coupling constants (approx. 11 Hz) and their chemical shifts are quite sensitive to the anisotropy of the SO moiety.