Synthesis of Trifluoromethyl Tetrafluoro‐λ6‐sulfanyl‐Substituted Alkenes, Ketones, and Acids: Polar Hydrophobic Building Blocks

Abstract

The trifluoromethyl tetrafluoro‐λ6‐sulfanyl (CF3SF4) group is both extraordinarily lipophilic and profoundly electron withdrawing, properties associated with polar hydrophobicity. Utilization of the CF3SF4 group to prepare novel materials or biologically active agents will not be possible without new methods for the synthesis of aliphatic CF3SF4‐substituted building blocks. To advance those studies, trichloromethanesulfenyl chloride was conveniently converted to trans‐trifluoromethyl tetrafluoro‐λ6‐sulfanyl chloride (CF3SF4Cl) by oxidative chlorofluorination. Triethylborane‐promoted addition reactions of trans‐CF3SF4Cl to substituted olefins and alkynes yielded a variety of new materials. Those addition products were subsequently transformed to CF3SF4‐substituted carboxylic acids, CF3SF4‐substituted ketones, and a CF3SF4‐substituted aldehyde.