Electrooxidative pinacol-type rearrangement of β-hydroxy sulfides. Efficient C-S cleavage mediated by chloride ion oxidation

Article abstract of DOI:10.1016/0040-4020(96)00130-5

Electrooxidation of α-phenyl substituted β-hydroxy sulfides in dichloromethane in the presence of chloride ions as the electrolyte results in a novel pinacol-type rearrangement to give 2-phenyl substituted ketones like 2-phenylcycloalkanone as the ring expansion product. The rearrangement is induced by an electrogenerated chloronium ion, which effects, instead of common C-C scission, a selective C-S cleavage of β-hydroxy sulfides.