Bromination and chlorination of 1,1,1-trifluoro-N-phenylmethanesulfonamides

Abstract

m/e 266 (M+), 338 (monosilylated product)4, 410 (disilylated product)4, 248 [monosilylated - (CHslgSiOH]4.

Trifluoromethanesulfonamide derivatives of azoles

“…Recently it was shown that a slight excess of fluorinated anhydride in the presence of excess of base was adequate for the formation of only mono-sulfonamides [16]. Trifluoromethanesulfonyl fluoride is known to give facile reactions with different amines yielding mono-sulfonamides [17]. In order to introduce the trifluoromethanesulfonyl moiety into Trifluoromethanesulfonamide-substituted azoles were synthesized by the reaction of 5-aminotetrazole, 3-amino-1,2,4-triazole and 3,5-diamine-1,2,4-triazole with trifluoromethanesulfonyl fluoride to prepare only monosubstituted compounds.…”

Trifluoromethanesulfonamides and Related Compounds

“…No N-halogenated products were obtained by chlorination or bromination of N -phenyltriflamide; instead, the halogenation occurred at the ortho and para positions of the aromatic ring. The reaction of N -phenyltriflamide with such electrophilic fluorinating reagents as fluoroxytrifluoromethane CF 3 OF and bis(fluoroxy)difluoromethane CF 2 (OF) 2 proceeds similarly .…”