Synthesis and structure of chiral palladium(II) complexes bearing ethylene-bridged bisindolinyl-and bis(1,2,3,4-tetrahydroquinolinyl) ligands

Journal of Organometallic Chemistry

Volumn 512, Issue 1-2, 1996, Pages 243-251

  Abu Surrah, Adnan S ^a   Fawzi, Riad ^a   Steimann, Manfred ^a   Rieger, Bernhard ^a,b  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b UNIVERSITY OF ULM   (Germany)

Author keywords

Bidentate ligands; Bridged complexes; Chirality; Crystal structure; Indolinyl ligands; Palladium

Indexed keywords

EID: 0030593215     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(95)05991-W     Document Type: Article

References (37)

1. s-symmetric species: (a) B. Rieger, X. Mu, D.T. Mallin, D.T. Rausch and J.C.W. Chien, Macromolecules, 23 (1990) 3559.
2. (b) W. Kaminsky, K. Külper, H.H. Brintzinger and F.R.W.P. Wild, Angew. Chem. Int. Ed. Engl., 24 (1985) 507.
3. (c) W. Röll, H.H. Brintzinger, B. Rieger and R. Zolk, Angew. Chem. Int. Ed. Engl., 102 (1990) 339.
4. (d) U. Stehling, J. Diebold, R. Kirsten, W. Röll, H.H. Brintzinger, S. Jüngling, R. Mülhaupt and F. Langhauser, Organometallics, 13 (1994) 964. Unsymmetric species:
5. (e) D.T. Mallin, M.D. Rausch, Y.G. Lin and J.C.W. Chien, J. Am. Chem. Soc., 12 (1990) 2030.
6. (f) J.C.W. Chien, B. Rieger, R. Sugimoto, D.T. Mallin and M.D. Rausch, Stud. Surf. Sci. Catal., 56 (1990) 535.
7. (g) B. Rieger, G. Jany, R. Fawzi and M. Steimann, Organometallics, 13 (1994) 647. For a review see: H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger and R. Waymouth, Angew. Chem., 107 (1995) 1255.
8. (g) B. Rieger, G. Jany, R. Fawzi and M. Steimann, Organometallics, 13 (1994) 647. For a review see: H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger and R. Waymouth, Angew. Chem., 107 (1995) 1255.
9. [2] (a) B.M. Trost, Acc. Chem. Res., 13 (1980) 3845.
10. (b) A. Togni, Tetrahedron Asymm., 2 (1991) 683, and references therein,
11. (c) W. Keim, H. Mass and S. Mecking, Z. Naturforsch. b, 50 (1995) 430.
12. (d) A. Sen, Acc. Chem. Res., 26 (1993) 303.
13. (e) V. Busico, P. Corradini, L. Landriani and M. Trifuoggi, Makromol. Chem. Rapid Commun., 14 (1993) 261.
14. (f) E. Drent, J.A.M. Van Brockhoeven and M.J. Doyle, J. Organomet. Chem., 417 (1991) 235.
15. (g) Z. Jiang, G.M. Dahlen, K. Houseknecht and A. Sen, Organometallics, 3 (1984) 866.
16. (h) W. Heitz, Angew. Makromol. Chem., 223 (1994) 135.
17. [3] (a) Z. Jiang, S.E. Adams and A. Sen, Macromolecules, 27 (1994) 2694.
18. (b) M. Brookhart and M.I. Wagner, J. Am. Chem. Soc., 116 (1994) 3641.
19. [4] F.Y. Xu, A.X. Zhao, J.C.W. Chien, Makromol. Chem., 194 (1993) 2579.
20. [5] B. Rieger, A.S. Abu-Surrah, R. Fawzi and M. Steimann, J. Organomet. Chem., 497 (1995) 73.
21. [6] This reaction is well known for the preparation of N,N′-diphenylethylene diamine and was adopted to our amines; cf. H.F. Morley, Chem. Ber., 12 (1879) 1793; for different procedures for the preparation of 3 and 4 see: (a) C.F. Nutaitis, Synth. Commun., 22 (1992) 1081. (b) W. Janssens, J.J. Vanheertum, J.R. Pollet, H.H. Sneyers and J.A. Dierckx, British Patent, 1 400 993; C.A. 83, 164018b, 1975.
22. [6] This reaction is well known for the preparation of N,N′-diphenylethylene diamine and was adopted to our amines; cf. H.F. Morley, Chem. Ber., 12 (1879) 1793; for different procedures for the preparation of 3 and 4 see: (a) C.F. Nutaitis, Synth. Commun., 22 (1992) 1081. (b) W. Janssens, J.J. Vanheertum, J.R. Pollet, H.H. Sneyers and J.A. Dierckx, British Patent, 1 400 993; C.A. 83, 164018b, 1975.
23. [6] This reaction is well known for the preparation of N,N′-diphenylethylene diamine and was adopted to our amines; cf. H.F. Morley, Chem. Ber., 12 (1879) 1793; for different procedures for the preparation of 3 and 4 see: (a) C.F. Nutaitis, Synth. Commun., 22 (1992) 1081. (b) W. Janssens, J.J. Vanheertum, J.R. Pollet, H.H. Sneyers and J.A. Dierckx, British Patent, 1 400 993; C.A. 83, 164018b, 1975.
24. 2-symmetric complexes mentioned here exist as racemic (rac) mixtures of enantiomers.
25. [8] (a) A. Sen and T.W. Lai, J. Am. Chem. Soc., 104 (1982) 3520;
26. (b) A. Sen and Z. Jiang, Macromolecules, 26 (1993) 911.
27. [9] The coordination of nitrate ions to Pd(II) metal centers was recently also reported by Krebs and co-workers; H. Engelking, S. Karentzopoullos, G. Reusmann and B. Krebs, Chem. Ber., 127 (1994) 2355.
28. [10] For the preparation of related amine allyl complexes cf. (a) L.S. Hegedus, B. Åkermark, D.J. Olsen, O.P. Anderson and K. Zetterberg, J. Am. Chem. Soc., 104 (1982) 697;
29. (b) N.W. Murrall and A.J. Welch, J. Organomet. Chem., 301 (1986) 109.
30. [11] A. Togni, G. Rihs, P.S. Pregosin and Ch. Ammann, Helv. Chim. Acta, 73 (1990) 723.
31. 2-symmetric form 'up' and 'down' positions cannot be distinguished.
32. [13] (a) cf. Ref. [10a].
33. (b) E. Benedetti, G. Maglio, R. Palumbo and C. Pedone, J. Organomet. Chem., 60 (1973) 189.
34. [14] J.R. Doyle, P.E. Slade and H.B. Jonassen, Inorg. Synth., 6 (1960) 216.
35. [15] B.M. Trost, P.E. Strege, L. Weber, T.J. Fullerton and T.J. Dietsche, J. Am. Chem. Soc., 100 (1978) 3407.
36. [16] For the analysis of coordinated nitrato ligands cf. also: J.R. Ferraro, Low Frequency Vibrations of Inorganic and Coordination Compounds, Plenum, New York, 1971, p. 79.
37. [17] Further details on the crystal structure investigation are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-58977, the names of the authors, and the journal citation.