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Unusual reactions of N-(trifluoromethylsulfonylimino)di-and-trifluoromethanesulfinimidoyl chlorides

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Abstract

N-(Trifluoromethylsulfonylimino)di-and-trifluoromethanesulfinimidoyl chlorides RS(=NSO2CF3)Cl (R = CF3, CHF2) react with potassium fluoride in 1,2-dimethoxyethane with formation of the corresponding N,N′-bis(trifluoromethylsulfonyl)fluoromethanesulfinimidamide potassium salts RS(=NSO2CF3)NSO2CF3 −K. Analogous methanesulfinimidoyl and fluoromethanesulfinimidoyl chlorides (R = CH3, CH2F) fail to react with KF under similar conditions. Treatment of trifluoromethanesulfenamides CF3SNR2 with N,N-dichlorotrifluoromethanesulfonamide CF3SO2NCl2 leads to N,N-disubstituted N′-(trifluoromethylsulfonyl)trifluoromethanesul-finimidamides CF3S(=NSO2CF3)NR2. The reaction of N,N-dimethyl-N′-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamide (R = CH3) with gaseous hydrogen chloride in diethyl ether gives sulfinimidoyl chloride CF3S(=NSO2CF3)Cl which could not be obtained by imination of CF3SCl.

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References

  1. Yagupol’skii, L.M., Popov, V.I., Pavlenko, N.V., Maletina, I.I., Mironova, A.A., Gavrilova, R.Yu., and Orda, V.V., Zh. Org. Khim., 1986, vol. 22, p. 2169.

    CAS  Google Scholar 

  2. Garlyauskajte, R.U., Sereda, S.V., and Yagupolskii, L.M., Tetrahedron, 1994, vol. 23, p. 6891.

    Article  Google Scholar 

  3. Garlyauskajte, R.U., Bezdudny, A.V., Michot, C., Armand, M., Yagupolskii, Y.L., and Yagupolskii, L.M., J. Chem. Soc., Perkin Trans. 1, 2002, p. 1887.

  4. Yagupolskii, Y.L., Bezdudnyi, A.V., and Yagupolskii, L.M., J. Fluorine Chem., 2002, vol. 115, p. 129.

    Article  CAS  Google Scholar 

  5. Yagupol’skii, Yu.L., Haas, A., Savina, T.I., Bezdudnyi, A.V., and Yagupol’skii, L.M., Russ. J. Org. Chem., 1999, vol. 35, p. 1766.

    CAS  Google Scholar 

  6. Yagupol’skii, L.M., Il’chenko, A.Ya., and Kondratenko, N.V., Usp. Khim., 1974, vol. 43, p. 64.

    CAS  Google Scholar 

  7. Moore, G., J. Org. Chem., 1979, vol. 44, p. 1708.

    Article  CAS  Google Scholar 

  8. Paquette, L., Wittenbrok, L., and Schreiber, K., J. Org. Chem., 1968, vol. 33, p. 1080.

    Article  CAS  Google Scholar 

  9. Lange, U. and Senning, A., Chem. Ber., 1991, vol. 124, p. 1879.

    CAS  Google Scholar 

  10. Garlyauskaite, R.Yu., Bisskii, G.V., and Yagupol’skii, L.M., Russ. J. Org. Chem., 1998, vol. 34, p. 1117.

    CAS  Google Scholar 

  11. Nazaretyan, V.P., Radchenko, O.A., and Yagupol’skii, L.M., Zh. Org. Khim., 1974, vol. 10, p. 2460.

    CAS  Google Scholar 

  12. Tullock, C.W. and Coffman, D.D., J. Org. Chem., 1960, vol. 25, p. 2016.

    Article  CAS  Google Scholar 

  13. Emeleus, H.J. and Nabi, S.N., J. Org. Chem., 1960, vol. 25, p. 1103.

    Article  Google Scholar 

  14. Kolasa, A. and Lieb, M., J. Fluorine Chem., 1995, vol. 70, p. 45.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine

    L. M. Yagupol’skii, A. V. Bezdudnyi & Yu. L. Yagupol’skii

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  1. L. M. Yagupol’skii
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  2. A. V. Bezdudnyi
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  3. Yu. L. Yagupol’skii
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Original Russian Text © L.M. Yagupol’skii, A.V. Bezdudnyi, Yu.L. Yagupol’skii, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1297–1300.

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Yagupol’skii, L.M., Bezdudnyi, A.V. & Yagupol’skii, Y.L. Unusual reactions of N-(trifluoromethylsulfonylimino)di-and-trifluoromethanesulfinimidoyl chlorides. Russ J Org Chem 42, 1275–1279 (2006). https://doi.org/10.1134/S1070428006090041

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  • DOI: https://doi.org/10.1134/S1070428006090041

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