N-fluoro-bis(trifluoromethanesulfonyl) imide. An improved synthesis

Synthesis of 3,6-dioxa-Δ7-4-trifluoromethyl perfluorooctyl trifluoromethyl sulfonimide: bis[(perfluoroalkyl)sulfonyl] superacid monomer and polymer

“…Previous work has shown that the reaction of sulfonyl fluorides with silylated sulfonamides yields the corresponding sulfonamide [17,[31][32][33]. This reaction offers a viable route to the synthesis of the perfluorinated sulfonimide monomer 16 in high yield from 9, CF 2 ¼CFOCF 2 CF(CF 3 )OCF 2 CF 2 SO 2 F. Since 9 was not readily available, it had to be synthesized before coupling with sodium trimethylsilyl trifluoromethyl sulfonamide 13.…”

“…Meubdoerffer and Neiderprum were the first to prepare bis((perfluoroalkyl)-sulfonyl)imides by reacting a sulfonyl fluoride with its sodium N-silyl form. In their route, the N-silyl was prepared by amination of the corresponding sulfonyl fluoride followed by neutralization then silyation [31][32][33]. Instead of preparing trifluoromethane sulfonamide 11 from the sulfonyl fluoride , the material can be synthesized from trifluormethane sulfonic anhydride 10 with ammonia [44,45].…”

Metal Triflimidates: Better than Metal Triflates as Catalysts in Organic Synthesis—The Effect of a Highly Delocalized Counteranion

“…The presence of two highly electron-withdrawing trifluoromethanesulfonyl groups on a nitrogen atom strongly increases the acidity of the N-bound hydrogen atom. [17,18] However, the relative acidities of HOTf and HNTf 2 are the subject of debate, with their out-of-range acidities only being estimated or measured indirectly. The gas-phase acidity of HNTf 2 (DG acid = 291.8 kcal mol À1 ) has been measured to be greater than that of HOTf (DG acid = 299.5 kcal mol À1 ).…”

Metalltriflimidate sind bessere Katalysatoren für die organische Synthese als Metalltriflate – der Effekt eines stark delokalisierten Gegenions

“…Die beiden stark elektronenziehenden Trifluormethansulfonyl-Substituenten erhöhen die Acidität des Wasserstoffatoms am Stickstoffatom außerordentlich. [17,18] Die relativen Aciditäten von HOTf und HNTf 2 werden noch diskutiert, da sie außerhalb des messbaren Bereichs liegen und geschätzt oder indirekt gemessen wurden. Für HNTf 2 wurde eine höhere Gasphasenacidität bestimmt als für HOTf (DG acid = 291.8 bzw.…”