Diastereoselectivity of chloride substitution reactions of cycloruthenated (R)c-(+)- and (S)c-(-)-dimethyl(1-phenylethyl)amine

Organometallics

Volumn 15, Issue 13, 1996, Pages 2932-2946

  Attar, Saeed ^a   Catalane, Vincent J ^a   Nelson, John H ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000253640     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960064b     Document Type: Article

References (81)

1. (a) Brunner, H. J. Organomet. Chem. 1969, 16, 119.
2. (b) Brunner, H. Angew. Chem., Int. Ed. Engl. 1969, 8, 382.
3. Bibler, J. P.; Wojcicki, A. Inorg. Chem. 1966, 5, 889.
4. (a) Brunner, H.; Schindler, H.-D.; Schmidt, E.; Vogel, M. J. Organomet. Chem. 1970, 24, 515.
5. (b) Ibid. 1970, 24, C7,
6. (c) Brunner, H.; Langer, M. J. Organomet. Chem. 1973, 54, 221.
7. (d) Brunner, H.; Aclasis, J.; Langer, M.; Steger, W. Angew. Chem., Int. Ed. Engl. 1979, 13, 810.
8. (a) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; Wiley: New York, 1994.
9. (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley-Interscience: New York, 1992.
10. (c) Hawkins, C. J. Absolute Configuration of Metal Complexes; Wiley: New York, 1971.
11. (d) Woldbye, F. In Technique of Inorganic Chemistry; Jonassen, H. B., Weissberger, A., Eds.; Interscience: New York, 1965; Vol. IV, pp 249-368.
12. (e) Saito, Y. Inorganic Molecular Dissymmetry; Inorganic Chemistry Concepts 4; Springer-Verlag: Berlin, 1979.
13. (f) Mason, S. F. Molecular Optical Activity and Chiral Discrimination; Cambridge University Press: Cambridge, U.K., 1982; Chapter 7.
14. (g) Sokolov, V. I. Chirality and Optical Activity in Organometallic Compounds; Gordon and Breach: New York, 1990.
15. (h) Kuroda, R.; Saito, Y. In Circular Dichroism, Principles and Applications; VCH: Weinheim, Germany, 1994; Chapter 9.
16. (a) Wojcicki, A. Adv. Organomet. Chem. 1973, 11, 87.
17. (b) Ibid. 1974, 12, 31.
18. (c) Flood, T. C.; Miles, D. L. J. Am. Chem. Soc. 1973, 95, 6460.
19. (d) Flood, T. C.; DiSanti, F. J.; Miles, D. L. Inorg. Chem. 1976, 15, 1910.
20. (e) Miles, S. L.; Miles, D. L.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1978, 100, 7278.
21. (f) Davison, A.; Martinez, N. J. Organomet. Chem. 1974, 74, C17.
22. (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauf, D. J. J. Am. Chem. Soc. 1975, 97, 2567.
23. (b) Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711.
24. (c) Kagan, H. B. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8, pp 463-498.
25. (a) Brunner, H. Acc. Chem. Res. 1979, 12, 251.
26. (b) Brunner, H. Adv. Organomet. Chem. 1980, 18, 151.
27. (c) Faller, J. W.; Shvo, Y. J. Am. Chem. Soc. 1980, 102, 5396.
28. (d) Quin, S.; Shaver, A.; Day, A. W. J. Am. Chem. Soc. 1982, 104, 1096.
29. (e) Faller, J. W.; Shvo, Y.; Chao, K.; Murray, H. H. J. Organomet. Chem. 1982, 226, 251.
30. (f) Brookhart, M.; Timmers, D.; Tucker, J. R.; Williams, G. D.; Husk, G. R.; Brunner, H.; Hammer, B. J. Am. Chem. Soc. 1983, 105, 6721.
31. (g) Merrifield, J. H.; Fernandez, J. M.; Buhro, W. E.; Gladyz, J. A. Inorg. Chem. 1984, 23, 4022 and references cited therein.
32. (h) Albers, M. O.; Robinson, D. J.; Singleton, E. Coord. Chem. Rev. 1987, 79, 1.
33. (i) Consiglio, G.; Morandini, F. Chem. Rev. 1987, 87, 761.
34. (j) Davies, S. G. Pure Appl. Chem. 1988, 60, 13.
35. (k) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
36. (a) Mandai, S. K.; Chakravarty, A. R. J. Organomet. Chem. 1991, 417, C59.
37. (b) Mandal, S. K.; Chakravarty, A. R. J. Chem. Soc., Dalton Trans. 1992, 1627.
38. (c) Mandai, S. K.; Chakravarty, A. R. Inorg. Chem. 1993, 32, 3851.
39. (d) Brunner, H.; Oeschey, R.; Nuber, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 866.
40. (e) Brunner, H.; Oeschey, R.; Nuber, B. Inorg. Chem. 1995, 34, 3349.
41. (a) LeBozec, H.; Touchard, D.; Dixneuf, P. H. Adv. Organomet. Chem. 1989, 8, 2863.
42. (b) Petrici, P.; Pitzalis, E.; Marchetti, F.; Rosini, C.; Salvadori, P.; Bennett, M. A. J. Organomet. Chem. 1994, 466, 221.
43. (c) Faller, J. W.; Chase, K. J. Organometallics 1995, 14, 1592.
44. (d) Luginbühl, W.; Zbinden, P.; Pittett, P. A.; Armbuster, T.; Burgi, H.-B.; Merbach, A. E.; Ludi, A. Inorg. Chem. 1991, 30, 2350.
45. Attar, S.; Nelson, J. H.; Fischer, J.; DeCian, A.; Sutter, J.-P.; Pfeffer, M. Organometallics 1995, 14, 4559.
46. Cesarotti, E.; Chiesa, A.; Ciani, G. F.; Sironi, A.; Vefghi, R.; White, C. J. Chem. Soc., Dalton Trans. 1984, 653.
47. (a) Howard, J.; Woodward, P. J. J. Chem. Soc., Dalton Trans. 1975, 59.
48. (b) Bennett, M. J.; Mason, R. Nature 1965, 205, 760.
49. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
50. (a) Van der Schaaf, P. A.; Boersma, J.; Kooijman, H.; Spek, A. L.; Van Koten, G. Organometallics 1993, 12, 4334.
51. (b) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395.
52. (c) Jiang, Q.; Rüegger, H.; Venanzi, L. M. J. Organomet. Chem. 1995, 488, 233. The first two citations claim that this conformation is rare, whereas the third claims that it is found approximately 50% of the time for such rings.
53. (a) Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
54. (b) Cahn, R. S.; Ingold, C.; Prelog. V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
55. (a) Attar, S.; Bearden, W. H.; Alcock, N. W.; Alyea, E. C.; Nelson, J. H. Inorg. Chem. 1990, 29, 425 and references cited therein.
56. (b) Nelson, J. H.; Mathey, F. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds.; VCH: Deerfield Beach, FL, 1987; pp 665-694.
57. (c) Mathey, F.; Fischer, J.; Nelson, J. H. Struct. Bonding (Berlin) 1983, 55, 153.
58. (d) Kessler, J. M.; Reeder, J.; Vac, R.; Yeung, C.; Nelson, J. H.; Frye, J. S.; Alcock, N. W. Magn. Reson. Chem. 1991, 29, S94.
59. (e) Attar, S.; Alcock, N. W.; Bowmaker, G. A.; Frye, J. S.; Bearden, W. H.; Nelson, J. H. Inorg. Chem. 1991, 30, 4166.
60. (f) Alyea, E. C.; Malito, J.; Attar, S.; Nelson, J. H. Polyhedron 1992, 11, 2409.
61. (g) Kessler, J. M.; Nelson, J. H.; Frye, J. S.; DeCian, A.; Fischer, J. Inorg. Chem. 1993, 32, 1048.
62. (h) Bowmaker, G. A.; Clase, H. J.; Alcock, N. W.; Kessler, J. M.; Nelson, J. H.; Frye, J. S. Inorg. Chim. Acta 1993, 210, 107.
63. (i) Holah, D. G.; Hughes, A. N.; Wright, K. Coord. Chem. Rev. 1975, 15, 239.
64. (a) Abbenhuis, H. C. L.; Pfeffer, M.; Sutter, J.-P.; DeCian, A.; Fischer, J.; Ji, H. -L.; Nelson, J. H. Organometallics 1993, 12, 4464.
65. (b) Pfeffer, M. Pure Appl. Chem. 1992, 64, 335.
66. Doxsee, K. M.; Hanawalt, E. M.; Shen, G. S.; Weakly, T. J. R.; Hope, H.; Knobler, C. B. Inorg. Chem. 1991, 30, 3381.
67. King, R. B.; Efraty, A. Inorg. Chem. 1969, 8, 2374.
68. Nelson J. H. Coord. Chem. Rev. 1995, 139, 245.
69. (a) McCormick, F. B.; Cox, D. D.; Gleason, W. B. Organometallics 1993, 12, 610.
70. (b) Seddon, E. A.; Seddon, K. R. The Chemistry of Ruthenium; Elsevier: Amsterdam, 1984; Chapter 9.
71. Sutter, J. -P. Ph.D. Dissertation, L'Université Louis Pasteur de Strasbourg, Strasbourg, France, 1992.
72. Morandini, F.; Consiglio, G.; Ciani, G.; Sironi, A. Inorg. Chim. Acta 1984, 82, L27.
73. (a) Hamon, P.; Toupet, L.; Hamon, J.-R.; Lapinte, C. Organometallics 1996, 15, 10.
74. (b) Hofmann, P. Angew. Chem., Int. Ed. Engl. 1977, 16, 536.
75. Katakis, D.; Gordon, G. Mechanisms of Inorganic Reactions', Wiley: New York, 1987.
76. Wolf, J.; Werner, H.; Serhadli, D.; Ziegler, M. L. Angew. Chem., Int. Ed. Engl. 1983, 22, 414.
77. Muetterties, E. L.; Bleeke, J. R.; Wucherer, E. J.; Albright, T. A. Chem. Rev. 1982, 82, 499.
78. O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307.
79. Affandi, S.; Green, R. L.; Hsieh, B. T.; Holt, M. S.; Nelson, J. H.; Alyea, E. C. Synth. React. Inorg. Met.-Org. Chem. 1987, 17, 307.
80. International Tables for X-ray Crystallography; D. Reidel: Boston, MA, 1992; Vol. C.
81. Flack, H. D. Acta Crystallogr. 1983, A39, 876.