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Synthesis of Neutral Dimethylaluminum Complexes Bearing Imino-Phenoxide Ligands
Corresponding Author(s) : Amer El-Batta
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
Synthesis of neutral dimethylaluminum complexes ligated by bidentate N,O salicylaldimine ligands is reported. Treatment of the imino-phenoxide ligands 3-R-2-(OH)C6H3CH=N(2,6-iPr2C6H3) [R = 9-anthracenyl (1a) and 1-naphthyl (1b)] with Al(CH3)3 in toluene affords the corresponding yellow dimethylaluminum compounds {3-R-2-(OH)C6H3CH=N(2,6-iPr2C6H3)}Al(CH3)2 [R = 9-anthracenyl (2a) and 1-naphthyl (2b)] in high yields. Reactions cleanly proceed by protodealumination of the Al-CH3 bond with concomitant elimination of methane. Toluene solutions of 2a-b, when activated with 1 equivalent of B(C6F5)3, polymerized ethylene to solid polyethylene with low activity.
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References
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(a) J.A. Ewen, J. Am. Chem. Soc., 106, 6355 (1984); (b) E.B. Coughlin and J.E. Bercaw, J. Am. Chem. Soc., 114, 7606 (1992); (c) X. Yang, C.L. Stern and T.J. Marks, J. Am. Chem. Soc., 116, 10015 (1994); (d) G.W. Coates and R.M. Waymouth, Science, 267, 217 (1995).
H. Makio, H. Terao, A. Iwashita and T. Fujita, Chem. Rev., 111, 2363 (2011).
(a) M.H. Chisholm and Z. Zhou, J. Mater. Chem., 14, 3081 (2004); (b) W. Hung and C. Lin, Inorg. Chem., 48, 728 (2009); (c) D. F.-J. Piesik, R. Stadler, S. Range and S. Harder, Eur. J. Inorg. Chem., 3569 (2009); (d) M.H. Chisholm, Pure Appl. Chem., 82, 1647 (2010).
(a) S. Brooker, Coord. Chem. Rev., 222, 33 (2001); (b) F.M. Bauers and S. Mecking, Angew. Chem. Int. Ed., 40, 3020 (2001); (c) B.-Y. Lee, G.C. Bazan, J. Vela, Z.J.A. Komon and X. Bu, J. Am. Chem. Soc., 123, 5352 (2001); (d) Y. Sunatsuki, Y. Motoda and N. Matsumoto, Coord. Chem. Rev., 226, 199 (2002); (e) R.T. Ruck and E.N. Jacobsen, J. Am. Chem. Soc., 124, 2882 (2002); (f) C.-M. Che and J.-S. Huang, Coord. Chem. Rev., 242, 27 (2003); (g) U. Beckmann and S. Brooker, Coord. Chem. Rev., 222, 17 (2003); (h) A. Pärssinen, T. Luhtanen, M. Klinga, T. Pakkanen, M. Leskelä and T. Repo, Eur. J. Inorg. Chem., 2100 (2005); (i) S. Adsule, V. Barve, D. Chen, F. Ahmed, Q.P. Dou, S. Padhye and F.H. Sarkar, J. Med. Chem., 49, 7242 (2006); (j) J.L. van Wyk, S. Mapolie, A. Lennartson, M. Hakansson and S. Jagner, Z. Naturforsch., 62b, 331 (2007); (k) T.W. Kim, U.R. Cho and D.H. Kim, Asian J. Chem., 25, 5297 (2013) (l) H. Khanmohammadi, S. Amani, H. Lang and T. Rueffer, Inorg. Chim. Acta, 360, 579 (2007); (m) P. DiBernardo, P.L. Zanonato, S. Tamburini and P.A. Vigato, Inorg. Chim. Acta, 360, 1083 (2007); (n) D.J. de Geest Andy Noble, B. Moubaraki, K.S. Murray, D.S. Larsen and S. Brooker, Dalton Trans., 467 (2007).
(a) S.N. Pal and S. Pal, Inorg. Chem., 40, 4807 (2001); (b) B. De Clercq and F. Verpoort, Macromolecules, 35, 894 (2002); (c) T. Opstal and F. Verpoort, Angew. Chem., Int. Ed., 42, 2876 (2003); (d) C. Carlini, S. Giaiacopi, F. Marchetti, C. Pinzino, A.M.R. Galleti and G. Sbrana, Organometallics, 25, 3659 (2006).
(a) J.W. Pyrz, A.I. Roe, L.J. Stern and J.R. Que, J. Am. Chem. Soc., 107, 614 (1985); (b) M. Tümer, B. Erdoðan, H. Koksal, S. Serin and M.Y. Nutku, Synth. React. Inorg. Met. Org. Chem., 28, 529 (1998).
(a) P.A. Cameron, V.C. Gibson, C. Redshaw, J.A. Segal, G.A. Solan, A.J.P. White and D.J. Williams, J. Chem. Soc., Dalton Trans., 1472 (2001); (b) D. Pappalardo, C. Tedesco and C. Pellecchia, Eur. J. Inorg. Chem., 621 (2002).
Y. Suzuki, H. Terao and T. Fujita, Bull. Chem. Soc. (Japan), 76, 1493 (2003).
D.J. Jones, V.C. Gibson, S.M. Green, P.J. Maddox, A. White and D.J. Williams, J. Am. Chem. Soc., 127, 11037 (2005).
(a) C.M. Wang, S. Friedrich, T.R. Younkin, R.T. Li, R.H. Grubbs, D.A. Bansleben and M.W. Day, Organometallics, 17, 3149 (1998); (b) T.R. Younkin, E.F. Conner, J.I. Henderson, S.K. Friedrich, R.H. Grubbs and D.A. Bansleben, Science, 287, 460 (2000); (c) X.F. Li and Y.S. Li, J. Polym. Sci. A: Polym. Chem., 40, 2680 (2002).
K.J. Duffy, A.N. Shaw, E. Delorne, S.B. Dillon, C. Erickson-Miller, L. Giampa, Y. Huang, R.M. Keenan, P. Lamb, N. Liu, S.G. Miller, A.T. Price, J. Rosen, H. Smith, K.J. Wiggall, L. Zhang and J.I. Luengo, J. Med. Chem., 45, 3573 (2002).