Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis and Reactivity of N-Trifluoromethyl-N-nitrosotrifluoromethanesulfonamide as a New Type of Trifluoromethylating Agent
Teruo UmemotoAkira Ando
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1986 Volume 59 Issue 2 Pages 447-452

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Abstract

N-Trifluoromethyl-N-nitrosotrifluoromethanesulfonamide (TNS-Tf) was synthesized in a 58% yield by the reaction of trifluoronitrosomethane with hydroxylamine followed by the treatment with trifluoromethanesulfonyl fluoride in the presence of a base. TNS-Tf was demonstrated to be an effective trifluoromethylating agent photochemically or thermally for aromatics, thiols, disulfides, and uridine derivatives. The insertion reaction by two trifluoromethyl groups of TNS-Tf to the sulfur-sulfur bonds was observed in the reaction with disulfides having electron-withdrawing groups, giving 2 mols of trifluoromethylthio compounds. Furthermore, TNS-Tf served as a good reagent for mild and convenient in situ generation of trifluoromethylcopper complex which converted iodoaromatics to trifluoromethyl-substituted aromatics in good yields. Similarly, N-trifluoromethyl-N-nitrosononafluoro-1-butanesulfonamide (TNS-Nf) was synthesized in a 36% yield. The examination of the reactivity indicated that this type of N-nitroso sulfonamides became to be sources of both perfluoroalkyl radicals contained.

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