Cyclic Alkoxyoxosulfonium Ions in the Chlorination of Hydroxy Sulfoxides

Abstract

Chlorination of β-, γ-, and δ-hydroxy sulfoxides with SO₂Cl₂ in CH₂Cl₂ at −78° resulted in the formation of the corresponding β-, γ-, and δ-chloro sulfones. Stereochemical evidence is presented that cyclic alkoxyoxosulfonium salts (O-alkylated sulfones) are intermediates in these transformations.