Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5, 5-dimethylhydantoin, vari
ous organic sulfides underwent a Pummerer-type rearrangement, followed by f
luorination, to give alpha-fluoro sulfides. The fluoro-Pummerer rearrangeme
nt, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe.
When an HF-pyridine reagent was used as the fluorinating agent, an oxidati
ve desulfurization-fluorination reaction occurred depending on the structur
e of the substrates.