Stepwise successive insertion of carbon monoxide and allenes into palladium-carbon bonds of complexes containing the rigid bidentate nitrogen ligand bis(p-anisylimino)acenaphthene

Organometallics

Volumn 15, Issue 15, 1996, Pages 3445-3455

  Groen, Johannes H ^a   Elsevier, Cornelis J ^a   Vrieze, Kees ^a   Smeets, Wilberth J J ^b   Spek, Anthony L ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001680178     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960163p     Document Type: Article

References (63)

1. Yamamoto, A. Organotransition Metal Chemistry; Wiley: New York, 1986.
2. Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8.
3. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books; Mill Valley, CA, 1987.
4. Cazes, B. Pure Appl. Chem. 1990, 62, 1867.
5. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247.
6. Drent, E.; van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
7. Sen, A.; Lai, T.-W. J. Am. Chem. Soc. 1982, 104, 3520.
8. Lai, T.-W.; Sen, A. Organometallics 1984, 3, 866.
9. Sen, A. Acc. Chem. Res. 1993, 26, 303.
10. Batistini, A.; Consiglio, G. Organometallics 1992, 11, 1766.
11. Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894.
12. Bartolini, S.; Carfagna, C.; Musco, A. Macromol. Rapid Commun. 1995, 16, 9.
13. Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1995, 117, 4455.
14. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663.
15. Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 1137.
16. Markies, B. A.; Verkerk, K. A. N.; Rietveld, M. H. P.; Boersma, J.; Kooijman, H.; Spek, A. L.; van Koten, G. J. Chem. Soc., Chem. Commun. 1993, 1317.
17. Markies, B. A.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A. N.; Boersma, J.; Kooijman, H.; Lakin, M. T.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1993, 117, 5263.
18. van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Elsevier, C. J. J. Chem. Soc., Chem. Commun. 1993, 1203.
19. van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
20. van Asselt, R.; Rijnberg, E.; Elsevier, C. J. Organometallics 1994, 13, 706.
21. Drent, E. Neth. Appl. 1988, 88/1168; Chem. Abstr. 1990, 113, 24686f.
22. Rülke, R. E.; Kliphuis, D.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; van Leeuwen, P. W. N. M.; Vrieze, K. J. Chem. Soc., Chem. Commun. 1994, 1817.
23. Rülke, R. E. Insertion Reactions with Novel Palladium Complexes; Dutch PhD Thesis; University of Amsterdam: Amsterdam, The Netherlands, 1995; pp 103-128.
24. van Asselt, R.; Elsevier, C. J.; Smeets, W. J. J.; Spek, A. L.; Benedix, R. Recl. Trav. Chim. Pays-Bas 1994, 113, 88.
25. Ankersmit, H. A.; Veldman, N.; Spek, A. L.; Eriksen, K.; Goubitz, K.; Vrieze, K.; van Koten, G. Inorg. Chim. Acta, in press.
26. Spek, A. L. J. Appl. Crystallogr. 1988, 21, 578.
27. Walker, N.; Stuart, D. Acta Crystallogr. 1983, A39, 158.
28. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System. Technical report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1992.
29. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C.
30. Sheldrick, G. M. SHELLXL93. Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Federal Republic of Germany, 1993.
31. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
32. Stevens, R. R.; Shier, G. D. J. Organomet. Chem. 1970, 21, 495.
33. Chrisholm, M. H.; Clark, H. C.; Hunter, D. H. J. Chem. Soc., Chem. Commun. 1971, 809.
34. Chrisholm, M. H.; Johns, W. S. Inorg. Chem. 1975, 14, 1189.
35. Clark, H. C.; Milne, C. R. C.; Wong, C. S. J. Organomet. Chem. 1977, 136, 265.
36. De Felice, V.; Cucciolito, M. E.; De Renzi, A.; Ruffo, F.; Tesauro, D. J. Organomet. Chem. 1995, 493, 1.
37. van Asselt, R.; Vrieze, K.; Elsevier, C. J. J. Organomet. Chem. 1994, 480, 27.
38. Crociani, B.; Boschi, T.; Uguagliati, P. Inorg. Chim. Acta 1981, 48, 9.
39. Crociani, B.; Di Bianca, F.; Giovenco, A.; Boschi, T. Inorg. Chim. Acta 1987, 127, 169.
40. The distance of the palladium atom from the plane defined by N(1), Cl(1) and the barycenter of the allyl triangle found in 7a (0.210-(1) Å) lies in between the value for an ideal square planar geometry (0 Å) and the calculated value for an ideal square pyramidal geometry (about 1.1 Å).
41. Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Akermark, B.; Cucciolito, M. E.; Giardano, F.; Vitagliano, A. Organometallics 1993, 12, 4940.
42. Fanizzi, F. P.; Maresca, L.; Natile, G.; Lanfranchi, M.; Tiripicchio, A.; Pacchioni, G. J. Chem. Soc., Chem. Commun. 1992, 333.
43. Albinati, A.; Kunz, R. W.; Ammann, C. J.; Pregosin, P. S. Organometallics 1991, 10, 1800.
44. Brumbaugh, J. S.; Whittle, R. R.; Parvez, M.; Sen, A. Organometallics 1990, 9, 1735.
45. Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357.
46. Gogoll, A.; Örnebro, J.; Grennberg, H.; Bäckvall, J.-E. J. Am. Chem. Soc. 1994, 116, 3631.
47. 3 gave sharp signals for both free and coordinated BIAN at 20 °C, indicating that ligand exchange is slower than the observed fluxional process.
48. Vrieze, K. In Dynamic Nuclear Magnetic Resonance Spectroscopy; Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975; pp 441-487.
49. Vrieze, K.; Volger, H. C.; van Leeuwen, P. W. N. M. Inorg. Chim. Acta Rev. 1969, 3, 109.
50. Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115.
51. Anderson, G. K.; Cross, R. J. J. Chem. Soc., Dalton Trans. 1979, 1246.
52. Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67.
53. Torn, D. L.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079.
54. Delis, J. G. P.; Groen, J. H.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Spek, A. L. To be published.
55. Also zerovalent palladium complexes containing monodentate coordinated rigid bidentate nitrogen ligands have been observed: (a) Klein, R. A.; Witte, P.; van Beizen, R.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; Numan, M. To be published. (b) Klein, R. A.; van Beizen, R.; Elsevier, C. J.; Fraanje, J.; Goubitz, K. To be published.
56. Also zerovalent palladium complexes containing monodentate coordinated rigid bidentate nitrogen ligands have been observed: (a) Klein, R. A.; Witte, P.; van Beizen, R.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; Numan, M. To be published. (b) Klein, R. A.; van Beizen, R.; Elsevier, C. J.; Fraanje, J.; Goubitz, K. To be published.
57. Oslinger, M.; Powell, J. Can. J. Chem. 1973, 51, 274.
58. Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598.
59. Hughes, R. P.; Powell, J. J. Organomet. Chem. 1973, 60, 409.
60. Ozawa, F.; Son, T.-i.; Osakada, K.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1989, 1067.
61. Hung, T.; Jolly, P. W.; Wilke, G. J. Organomet. Chem. 1980, 190, C5.
62. Santi, R.; Marchi, M. J. Organomet. Chem. 1979, 182, 117.
63. Behr, A.; Juszak, K.-D. J. Organomet. Chem. 1983, 255, 263.