Skip to main content
Log in

1,3,2-Diazasilols based on 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reduction of 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene (1, dpp-bian) in the presence of SiCl4 with two equivalents of potassium graphite (KC8) in tetrahydrofuran leads to the formation of compound (dpp-bian)SiCl2 (2), which was also synthesized by the exchange reaction of SiCl4 with the magnesium complex (dpp-bian)Mg(THF)3. An analog of compound 2, the bromo derivative (dpp-bian)SiBr2 (3), was obtained by the reaction of SiBr4 with one equivalent of Na2(dpp-bian) (in situ from Na and dpp-bian) in toluene. The silylene (dpp-bian)Si (4) was synthesized by the reduction of a mixture of dpp-bian and SiCl4 (1: 1) with four equivalents of potassium graphite in tetrahydrofuran. Treatment of compound 4 with diimine 1 gives the derivative (dpp-bian)2Si (5). Compounds 25 were characterized by 1H, 13C, and 29Si NMR spectroscopy, as well as by elemental analysis, their molecular structure was established by X-ray diffraction studies.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A. J. Arduengo, III, R. L. Harlow, M. Kline, J. Am. Chem. Soc., 1991, 113, 361.

    Article  CAS  Google Scholar 

  2. M. Denk, R. Lennon, R. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner, N. Metzler, J. Am. Chem. Soc., 1994, 116, 2691.

    Article  CAS  Google Scholar 

  3. W. A. Herrmann, M. Denk, J. Behm, W. Scherer, F. R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem., Int. Ed. Engl., 1992, 31, 1485.

    Article  Google Scholar 

  4. A. V. Zabula, F. E. Hahn, Eur. J. Inorg. Chem., 2008, 5165.

    Google Scholar 

  5. S. Nagendran, H. W. Roesky, Organometallics, 2008, 27, 457.

    Article  CAS  Google Scholar 

  6. M. Asay, C. Jones, M. Driess, Chem. Rev., 2011, 111, 354.

    Article  CAS  Google Scholar 

  7. S. K. Mandal, H. W. Roesky, Acc. Chem. Res., 2012, 45, 298.

    Article  CAS  Google Scholar 

  8. S. Khan, S. S. Sen, H. W. Roesky, Chem. Commun., 2012, 48, 2169.

    Article  CAS  Google Scholar 

  9. H. W. Roesky, J. Organomet. Chem., 2013, 730, 57.

    Article  CAS  Google Scholar 

  10. S. P. Kolesnikov, M. P. Egorov, A. S. Dvornikov, V. A. Kuz’min, O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2654 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1988, 37].

    Google Scholar 

  11. M. P. Egorov, O. M. Nefedov, T.-S. Lin, P. P. Gaspar, Organometallics, 1995, 14, 1539.

    Article  CAS  Google Scholar 

  12. S. E. Boganov, M. P. Egorov, O. M. Nefedov, Russ. Chem. Bull. (Engl. Transl.) 1999, 48, 98 [Izv. Akad. Nauk, Ser. Khim., 1999, 97].

    Article  CAS  Google Scholar 

  13. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, I. V. Krylova, O. M. Nefedov, R. Walsh, J. Am. Chem. Soc., 2002, 124, 7555.

    Article  CAS  Google Scholar 

  14. B. G. Kimelπ, V. V. Tumanov, V. I. Faustov, V. M. Promyslov, M. P. Egorov, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2002, 51, 1568 [Izv. Akad. Nauk, Ser. Khim., 2002, 1442].

    Article  Google Scholar 

  15. A. V. Lalov, S. E. Boganov, V. I. Faustov, M. P. Egorov, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2003, 52, 526 [Izv. Akad. Nauk, Ser. Khim., 2003, 504].

    Article  CAS  Google Scholar 

  16. S. E. Boganov, V. I. Faustov, M. P. Egorov, O. M. Nefedov, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 960 [Izv. Akad. Nauk, Ser. Khim., 2004, 920].

    Article  CAS  Google Scholar 

  17. R. Becerra, S. E. Boganov, M. P. Egorov, I. V. Krylova, O. M. Nefedov, R. Walsh, Chem. Phys. Lett., 2005, 413, 194.

    Article  CAS  Google Scholar 

  18. R. Becerra, S. E. Boganov, M. P. Egorov, V. I. Faustov, I. V. Krylova, O. M. Nefedov, V. M. Promyslov, R. Walsh, Phys. Chem. Chem. Phys., 2007, 4395.

    Google Scholar 

  19. S. E. Boganov, V. I. Faustov, K. N. Shavrin, V. D. Gvozdev, V. M. Promyslov, M. P. Egorov, O. M. Nefedov, J. Am. Chem. Soc., 2009, 131, 14688.

    Article  CAS  Google Scholar 

  20. R. Becerra, S. E. Boganov, M. P. Egorov, I. V. Krylova, V. M. Promyslov, R. Walsh, J. Am. Chem. Soc., 2012, 134, 10493.

    Article  CAS  Google Scholar 

  21. Y. Segawa, M. Yamashita, K. Nozaki, Science, 2006, 314, 113.

    Article  CAS  Google Scholar 

  22. Y. Wang, B. Quillian, P. Wei, C. S. Wannere, Y. Xie, R. B. King, H. F. Schaefer, III, P. v. R. Schleyer, G. H. Robinson, J. Am. Chem. Soc., 2007, 129, 12412.

    Article  CAS  Google Scholar 

  23. H. Braunschweig, R. Dewhurst, K. Hammond, J. Mies, K. Radacki, A. Vargas, Science, 2012, 336, 1419.

    Article  Google Scholar 

  24. S. P. Green, C. Jones, A. Stasch, Science, 2007, 318, 1754.

    Article  CAS  Google Scholar 

  25. S. P. Green, C. Jones, A. Stasch, Angew.Chem., Int. Ed., 2008, 47, 9079.

    Article  CAS  Google Scholar 

  26. J. Overgaard, C. Jones, A. Stasch, B. B. Iversen, J. Am. Chem. Soc., 2009, 131, 4208.

    Article  CAS  Google Scholar 

  27. Y. Liu, S. Li, X.-J. Yang, P. Yang, B. Wu, J. Am. Chem. Soc., 2009, 131, 4210.

    Article  CAS  Google Scholar 

  28. S. J. Bonyhady, C. Jones, S. Nembenna, A. Stasch, A. J. Edwards, G. J. McIntyre, Chem. Eur. J., 2010, 16, 938.

    Article  CAS  Google Scholar 

  29. C. Cui, H. W. Roesky, H.-G. Schmidt, M. Noltemeyer, H. Hao, F. Cimpoesu, Angew. Chem., Int. Ed., 2000, 39, 4274.

    Article  CAS  Google Scholar 

  30. X. Li, X. Cheng, H. Song, C. Cui, Organometallics, 2007, 26, 1039.

    Article  CAS  Google Scholar 

  31. S. J. Bonyhady, D. Collis, G. Frenking, N. Holzmann, C. Jones, A. Stasch, Nature Chemistry, 2010, 865.

    Google Scholar 

  32. Y. Zhao, Y. Liu, L. Yang, J.-G. Yu, S. Li, B. Wu, X.-J. Yang, Chem. Eur. J., 2012, 18, 6022.

    Article  CAS  Google Scholar 

  33. E. S. Schmidt, A. Jockisch, H. Schmidbaur, J. Am. Chem. Soc., 1999, 121, 9758.

    Article  CAS  Google Scholar 

  34. N. J. Hardman, B. E. Eichler, P. P. Power, Chem. Commun., 2000, 1991.

    Google Scholar 

  35. E. S. Schmidt, A. Schier, H. Schmidbaur, J. Chem. Soc., Dalton Trans., 2001, 505.

    Google Scholar 

  36. R. J. Baker, R. D. Farley, C. Jones, M. Kloth, D. M. Murphy, J. Chem. Soc., Dalton Trans., 2002, 3844.

    Google Scholar 

  37. C. Jones, P. C. Junk, J. A. Platts, A. Stasch, J. Am. Chem. Soc. 2006, 128, 2206.

    Article  CAS  Google Scholar 

  38. C. Jones, P. C. Junk, M. Kloth, K. M. Proctor, A. Stasch, Polyhedron, 2006, 25, 1592.

    Article  CAS  Google Scholar 

  39. C. Jones, R. P. Rose, A. Stasch, Dalton Trans., 2008, 2871.

    Google Scholar 

  40. J. Overgaard, C. Jones, D. Dange, J. A. Platts, Inorg. Chem., 2011, 50, 8418.

    Article  CAS  Google Scholar 

  41. G. Linti, T. Zessin, Dalton Trans., 2011, 40, 5591.

    Article  CAS  Google Scholar 

  42. G. Reeske, C. R. Hoberg, N. J. Hill, A. H. Cowley, J. Am. Chem., Soc. 2006, 128, 2800.

    Article  CAS  Google Scholar 

  43. S. Burck, D. Gudat, K. Nättinen, M. Nieger, M. Niemeyer, D. Schmid, Eur. J. Inorg. Chem., 2007, 5112.

    Google Scholar 

  44. G. Reeske, A. H. Cowley, Inorg. Chem., 2007, 46, 1426.

    Article  CAS  Google Scholar 

  45. C. A. Caputo, A. L. Brazeau, Z. Hynes, J. T. Price, H. M. Tuononen, N. D. Jones, Organometallics, 2009, 28, 5261.

    Article  CAS  Google Scholar 

  46. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, Angew. Chem., Int. Ed., 2003, 42, 3294.

    Article  CAS  Google Scholar 

  47. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, V. K. Cherkasov, G. K. Fukin, M. A. Lopatin, Eur. J. Inorg. Chem. 2004, 388.

    Google Scholar 

  48. I. L. Fedushkin, N. M. Khvoinova, A. V. Piskunov, G. K. Fukin, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 722 [Izv. Akad. Nauk, Ser. Khim., 2006, 697].

    Article  CAS  Google Scholar 

  49. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, S. Dechert, H. Schumann, Eur. J. Inorg. Chem., 2003, 3336.

    Google Scholar 

  50. I. L. Fedushkin, N. M. Khvoinova, A. A. Skatova, G. K. Fukin, Angew. Chem., Int. Ed., 2003, 42, 5223.

    Article  CAS  Google Scholar 

  51. I. L. Fedushkin, A. A. Skatova, V. K. Cherkasov, V. A. Chudakova, S. Dechert, M. Hummert, H. Schumann, Chem. Eur. J., 2003, 9, 5778.

    Article  CAS  Google Scholar 

  52. I. L. Fedushkin, A. G. Morozov, O. V. Rassadin, G. K. Fukin, Chem. Eur. J., 2005, 11, 5749.

    Article  CAS  Google Scholar 

  53. I. L. Fedushkin, V. M. Makarov, E. C. E. Rosenthal, G. K. Fukin, Eur. J. Inorg. Chem., 2006, 827.

    Google Scholar 

  54. I. L. Fedushkin, A. G. Morozov, M. Hummert, H. Schumann, Eur. J. Inorg. Chem., 2008, 1584.

    Google Scholar 

  55. H. Schumann, M. Hummert, A. N. Lukoyanov, I. L. Fedushkin, Organometallics, 2005, 24, 3891.

    Article  CAS  Google Scholar 

  56. A. N. Lukoyanov, I. L. Fedushkin, H. Schumann, M. Hummert, Z. Anorg. Allg. Chem., 2006, 632, 1471.

    Article  CAS  Google Scholar 

  57. A. N. Lukoyanov, I. L. Fedushkin, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2006, 55, 422 [Izv. Akad. Nauk, Ser. Khim., 2006, 409].

    Article  CAS  Google Scholar 

  58. H. Schumann, M. Hummert, A. N. Lukoyanov, I. L. Fedushkin, Chem. Eur. J., 2007, 13, 4216.

    Article  CAS  Google Scholar 

  59. I. L. Fedushkin, A. N. Lukoyanov, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1765 [Izv. Akad. Nauk, Ser. Khim. 2007, 1702].

    Article  CAS  Google Scholar 

  60. I. L. Fedushkin, A. A. Skatova, S. Y. Ketkov, O. V. Eremenko, A. V. Piskunov, G. K. Fukin, Angew. Chem., Int. Ed., 2007, 46, 4302.

    Article  CAS  Google Scholar 

  61. I. L. Fedushkin, A. N. Lukoyanov, S. Y. Ketkov, M. Hummert, H. Schumann, Chem. Eur. J., 2007, 13, 7050.

    Article  CAS  Google Scholar 

  62. I. L. Fedushkin, A. N. Lukoyanov, G. K. Fukin, S. Yu. Ketkov, M. Hummert, H. Schumann, Chem. Eur. J., 2008, 14, 8465.

    Article  CAS  Google Scholar 

  63. I. L. Fedushkin, A. N. Lukoyanov, A. N. Tishkina, G. K. Fukin, K. A. Lyssenko, M. Hummert, Chem. Eur. J., 2010, 16, 7563.

    Article  CAS  Google Scholar 

  64. I. L. Fedushkin, M. V. Moskalev, A. N. Lukoyanov, A. N. Tishkina, E. V. Baranov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 11264.

    Article  CAS  Google Scholar 

  65. I. L. Fedushkin, A. N. Lukoyanov, A. N. Tishkina, M. O. Maslov, S. Yu. Ketkov, M. Hummert, Organometallics, 2011, 30, 3628.

    Article  CAS  Google Scholar 

  66. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, N. M. Khvoinova, A. Yu. Baurin, S. Dechert, M. Hummert, H. Schumann, Organometallics, 2004, 23, 3714.

    Article  CAS  Google Scholar 

  67. I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin, G. K. Fukin, V. K. Cherkasov, M. P. Bubnov, Inorg. Chem., 2004, 43, 7807.

    Article  CAS  Google Scholar 

  68. M. Perego, G. Scarel, M. Fanciulli, I. L. Fedushkin, A. A. Skatova, Appl. Phys. Lett., 2007, 90, 162115/1.

    Article  CAS  Google Scholar 

  69. I. L. Fedushkin, N. M. Khvoinova, G. K. Fukin, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 612 [Izv. Akad. Nauk, Ser. Khim., 2009, 597].

    Article  CAS  Google Scholar 

  70. H. Tom Dieck, B. Bruder, K. D. Franz, Chem. Ber., 1983, 116, 136.

    Article  Google Scholar 

  71. H. Tom Dieck, M. Zettlitzer, Chem. Ber., 1987, 120, 795.

    Article  Google Scholar 

  72. H. H. Karsch, P. A. Schlueter, F. Bienlein, M. Herker, E. Witt, A. Sladek, M. Heckel, Z. Anorg. Allg. Chem., 1998, 624, 295.

    Article  CAS  Google Scholar 

  73. M. Driess, S. Yao, M. Brym, C. van Wüllen, D. Lentz, J. Am. Chem. Soc., 2006, 28, 9628.

    Article  Google Scholar 

  74. P. Zark, A. Schafer, A. Mitra, D. Haase, W. Saak, R. West, T. Muller, J. Organomet. Chem., 2010, 695, 398.

    Article  CAS  Google Scholar 

  75. L. Kong, J. Zhang, H. Song, C. Cui, Dalton Trans., 2009, 5444.

    Google Scholar 

  76. M. Haaf, A. Schmiedl, T. A. Schmedake, D. R. Powell, A. J. Millevolte, M. Denk, R. West, J. Am. Chem. Soc., 1998, 120, 12714.

    Article  CAS  Google Scholar 

  77. I. L. Fedushkin, V. A. Chudakova, G. K. Fukin, S. Dechert, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 2744 [Izv. Akad. Nauk, Ser. Khim., 2004, 2634].

    Article  CAS  Google Scholar 

  78. W. C. Schumb, R. C. Young, J. Am. Chem. Soc., 1930, 52, 1464.

    Article  CAS  Google Scholar 

  79. G. M. Sheldrick, SHELXTL v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.

    Google Scholar 

  80. G. M. Sheldrick, SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 1998.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. L. Fedushkin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2454–2461, Novemer, 2013.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fedushkin, I.L., Lukoyanov, A.N., Khvoinova, N.M. et al. 1,3,2-Diazasilols based on 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene. Russ Chem Bull 62, 2454–2461 (2013). https://doi.org/10.1007/s11172-013-0355-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-013-0355-z

Key word

Navigation