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Synthesis of N-[chloro(diorganyl)silyl]anilines

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Abstract

A series of N-[chloro(diorganyl)silyl]anilines RR′Si(NR″Ph)Cl (R, R′ = Me, Ph, CH2=CH, ClCH2, Cl(CH2)3; R″ = H, Me) was prepared via the reaction of diorganyldichlorosilanes with aniline or N-ethylaniline in the presence of triethylamine.

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References

  1. Wannagat, U., Adv. Inorg. Chem. Radiochem., 1964, vol. 6, p. 225.

    CAS  Google Scholar 

  2. Veith, M., Chem. Rev., 1990, vol. 90, no. 1, p. 3.

    Article  CAS  Google Scholar 

  3. Armitage, D.A., in The Chemistry of the Silicon-Heteroatom Bond, Patai, S. and Rappoport, Z., Eds., Chichester: Wiley, 1991, p. 365.

  4. Walter, S. and Klingebiel, U., Coord. Chem. Rev., 1994, vol. 130, nos. 1–2, p. 481.

    CAS  Google Scholar 

  5. Hemme, I. and Klingebiel, U., Adv. Organomet. Chem., 1996, vol. 39, p. 159.

    CAS  Google Scholar 

  6. Neugebauer, P., Jaschke, B., and Klingebiel, U., in The Chemistry of Organic Silicon Compounds, Rappoport, Z. and Apeloig, Y., Eds., Wiley, 2001, vol. 3, ch. 6, p. 429.

    Article  CAS  Google Scholar 

  7. Mo, Y., Zhang, Y., and Gao, J., J. Am. Chem. Soc., 1999, vol. 121, no. 24, p. 5737.

    Article  CAS  Google Scholar 

  8. Noodleman, L. and Paddock, N., L., Inorg. Chem., 1979, vol. 18, no. 2, p. 354.

    Article  CAS  Google Scholar 

  9. Bordeau, M., Frainnet, E., and Clement, C., J. Organometal. Chem., 1981, vol. 206, no. 1, p. 9.

    Article  CAS  Google Scholar 

  10. Mitzel, N.W., Angermaier, K., and Schmidbaur, H., Chem. Ber., 1994, vol. 127, no. 5, p. 841.

    Article  CAS  Google Scholar 

  11. Mitzel, N., Schier, A., and Schmidbaur, H., Chem. Ber., 1992, vol. 125, no. 12, p. 2711.

    Article  CAS  Google Scholar 

  12. Sujishi, S. and Witz, S., J. Am. Chem. Soc., 1954, no. 76, no. 18, p. 4631.

    Google Scholar 

  13. Pikies, J., Wojnowski, W., Popowski, E., and Kelling, H., Z. Anorg. Allg. Chem., 1978, vol. 447, no. 1, p. 199.

    Article  CAS  Google Scholar 

  14. Huber, G. and Schmidbaur, H., Z. Naturforsch. B, 1998, vol. 53, no. 10, p. 1103.

    CAS  Google Scholar 

  15. Burns, S.A., Corriu, R.J.P., Huynh, V., and Moreau, J.J., J. Organometal. Chem., 1987, vol. 333, no. 3, p. 281.

    Article  CAS  Google Scholar 

  16. Jacobson, M.A. and Williard, P.G., J. Org. Chem., 2002, vol. 67, no. 1, p. 32.

    Article  CAS  Google Scholar 

  17. Corriu, R.J.P., Moreau, J.J.E., and Vernhet, C., Tetrahedron Lett., 1987, vol. 28, no. 26, p. 2963.

    Article  CAS  Google Scholar 

  18. Corriu, R.J.P., Huynh, V., Iqbal, J., and Moreau, J.J.E., J. Organometal. Chem., 1984, vol. 276, no. 3, p. 61.

    Article  Google Scholar 

  19. Corriu, R.J.P., Perz, R., and Reye, C., Tetrahedron, 1983, vol. 39, no. 6, p. 999.

    Article  CAS  Google Scholar 

  20. Corriu, R.J.P., Huynh, V., and Moreau, J.J.E., Tetrahedron Lett., 1984, vol. 25, no. 18, p. 1887.

    Article  CAS  Google Scholar 

  21. Lukevics, E.Ya., Zablotskaya A.E., and Solomennikova, I.I., Russ. Chem. Rev., 1974, vol. 43, no. 2, p. 140.

    Article  Google Scholar 

  22. Kashutina, M.V., Ioffe, S.L., and Tartakovskii, V.A., Russ. Chem. Rev., 1975, vol. 44, no. 9, p. 733.

    Article  Google Scholar 

  23. Mizhiritskii, M.D. and Yuzhelevskii, Yu.A., Russ. Chem. Rev., 1987, vol. 56, no. 4, p. 355.

    Article  Google Scholar 

  24. Katsarava, R.D. and Vygodskii, Ya.S., Russ. Chem. Rev., 1992, vol. 61, no. 6, p. 629.

    Article  Google Scholar 

  25. Bleau, J.E., Carmalt, C.J., O’Neill, S.A., Parkin, I.P., White, A.J.P., and Williams, D.J., Polyhedron, 2005, vol. 24, no. 3, p. 463.

    Article  CAS  Google Scholar 

  26. Liu, X., Wu, Z., Cai, H., Yang, Y., Chen, T., Vallet, C.E., Zuhr, R.A., Beach, D.B., Peng, Z.-H., and Wu, Y.-D., J. Am. Chem. Soc., 2001, vol. 123, no. 33, p. 8011.

    Article  CAS  Google Scholar 

  27. Hasan, P., Potts, S.E., Carmalt, C.J., Palgrave, R.G., and Davies, H.O., Polyhedron, 2008, vol. 27, no. 3, p. 1041.

    Article  CAS  Google Scholar 

  28. Cheng, F., Clark, S., Kelly, S.M., Bradley, J.S., and Lefebvre, F., J. Am. Ceramic Soc., 2004, vol. 87, no. 8, p. 1413.

    Article  CAS  Google Scholar 

  29. Yong-Jae, C., Uk, H., and Tzy-Jiun, M.L., J. Sol-Gel Sci. Technol., 2009, vol. 51, no. 1, p. 124.

    Article  Google Scholar 

  30. Cheng, F., Kelly, S.M., Clark, S., Bradley, J.S., Baumbach, M., and Schuetze, A., J. Membr. Sci., 2006, vol. 280, nos. 1–2, p. 530.

    Article  CAS  Google Scholar 

  31. Lazareva, N.F., Vakul’skaya, T.I., and Lazarev, I.M., J. Phys. Org. Chem., 2009, vol. 22, no. 2, p. 144.

    Article  CAS  Google Scholar 

  32. Lazareva, N.F., Brodskaya, E.I., and Ratovski, G.V., J. Chem. Soc., Perkin Trans. 2, 2002, no. 12, p. 2083.

    Google Scholar 

  33. Yunjun, W., Shaowu, W., Lijun, Z., Gaosheng, Y., Xiancui, Z., Zhihong, Z., Hong, Z., and Shihong, W., Eur. J. Org. Chem., 2010, no. 2, p. 326.

    Google Scholar 

  34. Yunjun, W., Shaowu, W., Xiancui, Z., Gaosheng, Y., Yun, W., Lijun, Z., and Haibin, S., Inorg. Chem., 2008, vol. 47, no. 12, p. 5503.

    Article  Google Scholar 

  35. Niederpruem, H. and Simmler, W., Chem. Ber., 1963, vol. 96, no. 4, p. 965–75.

    Article  CAS  Google Scholar 

  36. Wieber, M. and Schmidt, M., J. Organometal. Chem., 1963, vol. 1, no. 1, p. 22.

    Article  CAS  Google Scholar 

  37. George, P.D., Prober, M., and Eliott, J.R., Chem. Rev., 1956, vol. 56, no. 6, p. 1065.

    Article  CAS  Google Scholar 

  38. Picard, J.-P., Adv. Organomet. Chem., 2005, vol. 52, p. 175.

    CAS  Google Scholar 

  39. Yoder, C.H., Ryan, C.M., Martin, G.F., and Ho, P.S., J. Organometal. Chem., 1980, vol. 190, no. 1, p. 1.

    Article  CAS  Google Scholar 

  40. Fryzuk, M.D., Johnson, S.A., and Rettig, S.J., J. Am. Chem. Soc., 1998, vol. 120, no. 42, p. 11024.

    Article  CAS  Google Scholar 

  41. Fryzuk, M.D., Johnson, S.A., Patrick, B.O., Albinati, A., Mason, S.A., and Koetzle, T.F., J. Am. Chem. Soc., 2001, vol. 123, no. 17, p. 3960.

    Article  CAS  Google Scholar 

  42. Eisch, J.J. and Chiu, C.S., Heteroat. Chem., 1994, vol. 5, no. 3, p. 265.

    Article  CAS  Google Scholar 

  43. Kozyukov, V.P. and Mironov, V.F., Zh. Obshch. Khim., 1974, vol. 44, no. 3, P. 553.

    CAS  Google Scholar 

  44. Wannagat, U. and Schreiner, G., Monatsh. Chem., 1965, vol. 96, no. 6, p. 1889.

    Article  CAS  Google Scholar 

  45. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

    Google Scholar 

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. Yu. Nikonov, I. V. Sterkhova & N. F. Lazareva

Authors
  1. A. Yu. Nikonov
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  2. I. V. Sterkhova
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  3. N. F. Lazareva
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Corresponding author

Correspondence to N. F. Lazareva.

Additional information

Original Russian Text © A.Yu. Nikonov, I.V. Sterkhova, N.F. Lazareva, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 789–793.

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Nikonov, A.Y., Sterkhova, I.V. & Lazareva, N.F. Synthesis of N-[chloro(diorganyl)silyl]anilines. Russ J Gen Chem 84, 883–887 (2014). https://doi.org/10.1134/S107036321405017X

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  • DOI: https://doi.org/10.1134/S107036321405017X

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