Unexpected outcome in the reaction of tetrakis(dimethylamino)ethylene (TDAE) with bis(difluoromethyl)disulfide.

Abstract

In an attempt to generate a reactive nucleophilic source of the difluoromethylthio group, an unexpected outcome was obtained in the reaction of tetrakis(dimethylamino)ethylene (TDAE) with bis(difluoromethyl)disulfide (HCF₂SSCF₂H). Although the TDAE²⁺(HCF₂S^-)₂ intermediate appeared to be formed, it proved insufficiently reactive to be alkylated by benzyl bromide and other activated alkyl bromides. Instead, the intermediate lost the fluoride ion to form SCHF, which then proceeded to convert to two unexpected products, which were characterized using spectroscopic tools and X-ray analysis.