Abstract
Procedures are reported for the conversion of 2,3-epoxysulfides to 3-hydroxy-1,2-dithioethers. Conventional nucleophilic ring opening using a thiolate gives a mixture of products resulting from ring opening at C-2 and C-3, with the latter predominating. With sodium thiolates in DMF a competing β-elimination process is observed to form 3-hydroxy-1-alkenylthioethers. Alternatively, Lewis acid induced thiiranium ion generation from a 2,3-epoxy sulfide, and nucleophilic ring opening with S-trimethylsilylthiophenol gives 3-hydroxy-1,2-dithioethers with full regio- and stereo-control.
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