Synthesis and structure of N-(diaminomethylidene)- and N-[bis(cyclohexylamino)methylidene]trifluoromethanesulfonamides

N-Trifluoromethylsulfonyl-substituted guanidines CF3SO2N=C(NHR)2 (R = H, cyclohexyl) were synthesized in nearly quantitative yield by reactions of N-sulfinyltrifluoromethanesulfonamide CF3SO2N=S=O with urea and of trifluoromethanesulfonamide with N,N′-dicyclohexylcarbodiimide. N-[Bis(cyclohexylamino)-methylidene]trifluoromethanesulfonamide was subjected to protonation with trifluoromethanesulfonic acid and bis(trifluoromethanesulfonyl)imide, and the structure of the resulting salts and initial N-trifluoromethylsulfonylguanidines was studied by NMR and IR spectroscopy and DFT quantum-chemical calculations.