Abstract
N-Sulfinyltrifluoromethanesulfonamide CF3SO2N=S=O reacts with salicylaldehyde, 2-furaldehyde, 2-thiophenecarbaldehyde, 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, and 2-phenyl-2H-1,2,3-triazole-4-carbaldehyde to afford the corresponding N-aryl(hetaryl)methylidenetrifluoromethanesulfonamides in high yields. Reactions of the latter with aniline give no adducts at the C=N bond but transamination products. The reaction of trifluoromethanesulfonamide with phenyl isocyanate led to formation of N,N′-diphenylurea instead of expected N-phenyl-N′-(trifluoromethylsulfonyl)urea.
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REFERENCES
Yagupol’skii, L.M., Popov, V.I., Pavlenko, N.V., Maletina, I.I., Mironova, A.A., and Gavrilova, R.Yu., Zh. Org. Khim., 1986, vol. 22, p. 2169.
Behrend, E. and Haas, A., J. Fluorine Chem., 1974, vol. 4, p. 83.
Zhu, S.Z., Lee, A.W., Zhu, Y.H., Chen, X.M., Dai, J.N., and Yuan, X.W., J. Fluorine Chem., 1993, vol. 60, p. 283.
Zhu, S.Z. and Jin, X.L., J. Fluorine Chem., 1995, vol. 72, p. 19.
Kresze, G., Maschke, A., Albrecht, R., Bederke, K., Patzschlze, M.P., Smalla, M., and Trede, A., Angew. Chem., 1962, vol. 74, p. 135.
Albrecht, R., Kresze, G., and Mlakar, B., Chem. Ber., 1964, vol. 97, p. 483.
Kresze, G. and Wucherpfennig, W., Angew. Chem., 1967, vol. 79, p. 109.
Levkovskaya, G.G., Drozdova, T.I., Rozentsveig, I.B., and Mirskova, A.N., Usp. Khim., 1999, vol. 68, p. 638.
Audoye, P., Coumes, R-C., Gaset, A., and Gorrichon, J-P., Can. J. Chem., 1982, vol. 60, p. 1148.
Iovel’, I., Golomba, L., Popelis, Yu., and Lukevits, E., Khim. Geterotsikl. Soedin., 2002, p. 51.
Bratenko, M.K., Chernyuk, I.N., and Vovk, M.V., Russ. J. Org. Chem., 1997, vol. 33, p. 1293.
Kira, M.A., Abdel-Rahman, and Gadalla, K.Z., Tetrahedron Lett., 1969, p. 109.
Meshcheryakov, V.I., Shainyan, B.A., Tolstikova, L.L., and Albanov, A.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1517.
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 1006–1010.
Original Russian Text Copyright © 2005 by Shainyan, Tolstikova.
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Shainyan, B.A., Tolstikova, L.L. Reaction of N-Sulfinyltrifluoromethanesulfonamide CF3SO2N=S=O with Carbonyl Compounds. Russ J Org Chem 41, 984–988 (2005). https://doi.org/10.1007/s11178-005-0281-0
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DOI: https://doi.org/10.1007/s11178-005-0281-0