ATSynthesis and reactions of ω-CF3O-substituted aliphatic sulfonyl chlorides

ABSTRACT A two-step approach to the synthesis of ω-CF3O-substituted aliphatic sulfonyl chlorides is reported. The method is based on the reaction of alkylating agents bearing a ω-CF3O substituent with thiourea and subsequent oxidative chlorination of the obtained isothiuronium salt. In this way, β-(trifluoromethoxy)ethane and γ-(trifluoromethoxy)propane sulfonyl chlorides were obtained and assessed as the reagents in the sulfonylation reaction with amines. The former one participated the reaction affording the corresponding vinylsulfonamides because of β-elimination of trifluoromethanol, while the latter one allowed for the preparation of desired γ-(trifluoromethoxy)propane sulfonamides.