The reactions of the trifluoromethyl disulfide group, CF3SS—, with ammonia and amines. A new preparation of sulfenamides

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Abstract
Bistrifluoromethyl disulfide reacts with ammonia and primary and secondary amines, forming the compounds CF3SNH2, RNHSCF3, and R2NSCF3, respectively; also produced are ammonium fluoride and thiocyanate, or a substituted thiourea and hydrogen fluoride, which forms a salt with the amine or thiourea.Simple sulfenamides, RSNH2, can be prepared from ammonia and a trifluoromethyl disulfide, RSSCF3; ammonium fluoride and thiocyanate are also produced. Since the trifluoromethyl disulfides are formed from thiols and trifluoromethanesulfenyl chloride, the reaction offers a simple method for the conversion of thiols into sulfenamides.The new compounds N-propyltrifluoromethanesulfenamide, N,N-diethyltrifluoromethanesulfenamide, bispentafluorobenzenesulfenimide, pentafluorophenyltrifluoromethyl disulfide, and n-propyltrifluoromethyl disulfide have been prepared and characterized.