The first bis(perfiuoroalkyl)sulfur oxyimines, (CF3)2S(0)NH, CF3(C2Fa)S(0)NH, and (C2F5)2S(0)NH, have been synthesized by the reaction of ammonia with bis(perfluoroalkyl)sulfiir oxydifluorides. As typical of the compounds in the above series, the reactions of bis(trifluoromethyl)sulfur oxyimine have been investigated to produce the new compounds (CF3)2-S(0)NSCF3, (CF3)2S(0)NCN, (CF3)2S(0)NS(0)CF3, (CF3)2S(0)NC(0)CF3, (CF3)2S(0)NSi(CH3)3, and AgNS(0)(CF3)2.The last compound reacts with CH3I and CU to give (CF3)2S(0)NCH3 and (CF3)2S(0)NC1. With the exception of the silver salt which is a solid, these compounds are colorless liquids which have been characterized by infrared, nmr, and mass spectra as well as elemental analyses and vapor pressure data.Recently there has been considerable interest in the chemistry of compounds containing the sulfur oxyimine moiety >S 3 N-are grateful to Mr. R. A. De Marco for mass spectra. J. M. S. thanks the Alfred P. Sloan Foundation for a fellowship.
Trifluoromethylsulfinate esters and trifluoromethylsulfinamides result when trifluoromethylsulfinyl fluoride reacts with alcohols and amines Mercaptans with CFpS(0)F do not yield the expected thiosulfinates but rather mixed disulfides. The methylene protons of CFpCHxOS(0)CFp and CHaCH*OS( O)CF, are magnetically nonequivalent giving rise to ABMJ-X3 nmr spectra. The new compounds CF3S(O)OCHa, CFBS(O)OCHLCHB, CFpS(0)OCHaCFp, CF,S(O)X( CH2CHs)%, CF3S(0)N( CH3)2, (CFpS(0))2NCHp, and CFpS(O)KH2 are slightly volatile, colorless liquids. JB-M~ = 7.0 JB-x = 1.5 JA-B = 9.8 JA-B = 10.0 J A -x~ = 0.6 J A -M~ = 7.3 J B -x~ = 1 , l JB-M~ = 7.1 JA-B = 12.6 J A -x~ = 0.6 JA-M, = 7.9 J B -X , = 1.0 JB-M~ = 7.6 J M~--X~ = 0.7 JA~-M, = 7.2 JA,-x, = 0.8 L o g P m m = ASv, CONTRIBUTION FROM THE DEPARTMENT OF CHEMISTRY,
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