N,N'-Bis(trifluoromethanesulfonyl)oxamide

摘要

It is known that sulfonamides RSO_2NH_2 react with oxalyl chloride both by way of substitution to give bis(sulfonyl)oxamides RSO_2NHC(O)C(O)NHSO_2R and in a more complicaated fashion, with decarbonylation and cyclization, to form sulfonyl isocyanates RSO_2NCO and parbanic acid derivatives [1]. The same reaction with trifluoromethanesulfonamide CF_3SO_2NH_2 would be expected to give the oxamide CF_3SO_2NHCOCONHSO_2CF_3 (I) which is a strong NH acid. Lithium salts of such acids are used as ionogenic additives to nonaqueous electrolytes in chemical sources of current [2,3]. We found that compound I is formed by the reaction of sodium trifluoromethane-sufonamide and oxalyl chloride. The structure of the reaction product was confirmed by its ~1H, ~13C, and ~19F NMR and IR spectra and elemental analysis.