Skip to main content
SpringerLink
Log in

Reduction of aromatic ketones with the (dpp-BIAN)AlI(Et2O) complex

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reduction of benzophenone and 4,4′-bis(methoxy)benzophenone with the aluminum complex (dpp-BIAN)AlI(Et2O) (1) containing the dianionic dpp-BIAN ligand (dpp-BIAN is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) affords the pinacolate complexes [(dpp-BIAN)AlI]2[μ-O2C2Ph4] (2) and [(dpp-BIAN)AlI]2[μ-O2C2(C6H4OMe)4] (3), respectively, which undergo the pinacolone rearrangement upon prolonged storage in diethyl ether to form [(dpp-BIAN)AlI]2O (4). The reaction of 1 with fluoren-9-one produces stable pinacolate (dpp-BIAN)Al[μ-O2(C13H8)2] (7) and the (dpp-BIAN)AlI2 complex (8). Compounds 2—4, 7, and 8 were characterized by ESR spectroscopy. Hydrolysis products of compounds 2 and 3 were characterized by 1H NMR spectroscopy. The structures of complexes 4 and 7 were established by X-ray diffraction.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. M. W. van Laren and C. J. Elsevier, Angew. Chem., Int. Ed., 1999, 38, 3715.

    Article  Google Scholar 

  2. R. van Belzen, H. Hoffmann, and C. J. Elsevier, Angew. Chem., Int. Ed., 1997, 36, 1743; (b) G. A. Grasa, R. Singh, E. D. Stevens, and S. P. Nolan, J. Organomet. Chem., 2003, 687, 269.

    Article  Google Scholar 

  3. A. Heumann, L. Giordano, and A. Tenaglia, Tetrahedron Lett., 2003, 44, 1515.

    Article  CAS  Google Scholar 

  4. J. W. Sprengers, M. de Greef, M. A. Duin, and C. J. Elsevier, Eusr. J. Inorg. Chem., 2003, 3811.

  5. E. Cherian, E. B. Lobkovsky, and G. W. Coates, Chem. Commun., 2003, 20, 2566; (b) F. Al-Abaidi, Z. Ye, and S. Zhu, Macromol. Chem. Phys., 2003, 204, 1653; (c) V. Fassina, C. Ramminger, M. Seferin, R. S. Mauler, R. F. de Souza, and A. L. Monteiro, Macromol. Rapid Commun., 2003, 24, 667; (d) M. D. Leatherman, S. A. Svejda, L. K. Johnson, and M. Brookhart, J. Am. Chem. Soc., 2003, 125, 3068.

    Article  Google Scholar 

  6. I. Kim, J.-M. Hwang, J. K. Lee, C. S. Ha, and S. I. Woo, Macromol. Rapid Commun., 2003, 24, 508.

    Article  CAS  Google Scholar 

  7. J. Kiesewetter and W. Kaminsky, Chem. Eur. J. 2003, 9, 1750.

    Article  CAS  Google Scholar 

  8. D. Takeuchi, A. Yasuda, and K. Osakada, Dalton Trans., 2003, 2029.

  9. B. Binotti, C. Carfagna, C. Zuccaccia, and A. Macchioni, Chem. Commun., 2005, 92.

  10. B. S. Williams, M. D. Leatherman, P. S. White, and M. Brookhart, J. Am. Chem. Soc., 2005, 127, 5132; (b) J. Merna, J. Cihlar, M. Kucera, A. Deffieux, and H. Cramail, Eur. Polym. J., 2005, 41, 303; (c) W. Liu and M. Brookhart, Organometallics, 2004, 23, 6099; (d) D. H. Camacho, E. V. Salo, J. W. Ziller, and Z. Guan, Angew. Chem., Int. Ed., 2004, 43, 1821.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, S. Dechert, and H. Schumann, Eur. J. Inorg. Chem., 2003, 3336; (b) I. L. Fedushkin, A. G. Morozov, O. V. Rassadin, and G. K. Fukin, Chem. Eur. J., 2005, 11, 5749.

    Google Scholar 

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

    Google Scholar 

  14. H. Schumann, M. Hummert, A. N. Lukoyanov, and I. L. Fedushkin, Organometallics, 2005, 24, 3891; (b) A. N. Lukoyanov, I. L. Fedushkin, M. Hummert, and H. Schumann, Z. Anorg. Allg. Chem., 2006, 632, 1471.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin, G. K. Fukin, V. K. Cherkasov, and M. P. Bubnov, Inorg. Chem., 2004, 43, 7807; (b) I. L. Fedushkin, N. M. Khvoinova, A. Yu. Baurin, V. A. Chudakova, A. A. Skatova, V. K. Cherkasov, G. K. Fukin, and E. V. Baranov, Izv. Akad. Nauk, Ser. Khim., 2006, 71 [Russ. Chem. Bull., Int. Ed., 2006, 55 74].

    Article  CAS  Google Scholar 

  17. I. L. Fedushkin, A. A. Skatova, A. N. Lukoyanov, V. A. Chudakova, S. Dechert, M. Hummert, and H. Schumann, Izv. Akad. Nauk, Ser. Khim., 2004, 2641 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2751]; (b) I. L. Fedushkin, V. M. Makarov, E. C. E. Rosenthal, and G. K. Fukin, Eur. J. Inorg. Chem., 2006, 827.

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

    Article  CAS  Google Scholar 

  19. I. L. Fedushkin, A. A. Skatova, G. K. Fukin, M. Hummert, and H. Schumann, Eur. J. Inorg. Chem., 2005, 2332.

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

    Article  CAS  Google Scholar 

  21. N. Kuhn, S. Fuchs, E. Niquet, M. Richter, and M. Steimann, Z. Anorg. Allg. Chem., 2002, 628, 717.

    Article  CAS  Google Scholar 

  22. G. M. Sheldrick, SADABS Program for Empirical Absorption Correction of Area Detector Data, Universität Göttingen, Göttingen (Germany), 1996.

    Google Scholar 

  23. G. M. Sheldrick, SHELXS-97 Program for the Solution of Crystal Structures, Universität Göttingen, Göttingen (Germany), 1990.

    Google Scholar 

  24. G. M. Sheldrick, SHELXL-97 Program for the Ref inement of Crystal Structures, Universität Göttingen, Göttingen (Germany), 1997.

    Google Scholar 

  25. K. Brandenburg, Diamond Version 2.1c, Institut für Anorganische Chemie Universität Kiel, 1999.

Download references

Author information

Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhnii Novgorod, Russian Federation

    I. L. Fedushkin, A. N. Lukoyanov & G. K. Fukin

  2. Institute of Chemistry, Technical University of Berlin, 135 Strasse des 17 Juni, D-10623, Berlin, Germany

    M. Hummert & H. Schumann

Authors
  1. I. L. Fedushkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. N. Lukoyanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. K. Fukin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Hummert
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. Schumann
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

dpp-BIAN is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1134–1140, July, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fedushkin, I.L., Lukoyanov, A.N., Fukin, G.K. et al. Reduction of aromatic ketones with the (dpp-BIAN)AlI(Et2O) complex. Russ Chem Bull 55, 1177–1183 (2006). https://doi.org/10.1007/s11172-006-0396-7

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-006-0396-7

Key words

Search

Navigation