Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

Article abstract of DOI:10.1246/bcsj.71.2687

Upon treatment with n-Bu₄NH₂F₃ and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF₂SMe, gave trifluoro sulfides RCF(SMe)CF₂SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.