Organometallic helices: The mechanism of formation of "metallospiralenes"

Organometallics

Volumn 19, Issue 25, 2000, Pages 5484-5499

  Djukic, Jean Pierre ^a   Aline, Maisse Francüois ^a   Michel, Pfeffer ^a   Dötz, Karl Heinz ^a,b   Cian, André De ^a   Fischer, Jean ^a  

^a CNRS   (France)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; CHEMICAL BONDS; ISOMERS; MANGANESE COMPOUNDS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION ANALYSIS;

CARBENE CARBON ATOM; METALLOSPIRALENES; ORGANOMETALLIC HELICES; STEREOSELECTIVITY;

ORGANOMETALLICS;

EID: 0034506556     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0006920     Document Type: Article

References (87)

1. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis, Targets, Strategies, Methods; VCH-Verlag: Weinheim, 1996.
2. (a) Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. (b) Tour, J. M. Chem. Rev. 1996, 96, 537.
4. (c) Shell, A. J. Chem. Rev. 1996, 96, 195.
5. (d) Ho T.-L. Stereoselectivity in Organic Synthesis; Wiley: New York, 1999.
6. (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
7. (b) Dötz, K. H.; Pfeiffer, J. Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1.
8. (c) Gleichmann, M. M.; Dötz, K. H.; Hess, B. A. J. Am. Chem. Soc. 1996, 118, 10551.
9. (d) Hohmann, F.; Siemoneit, S.; Nieger, M.; Kotila, S.; Dötz, K. H. Chem. Eur. J. 1997, 3, 853.
10. (d) Dötz, K. H.; Stinner, C. Tetrahedron Asym. 1997, 8, 1751.
11. (e) Pfeiffer, J.; Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2828.
12. (f) Longen, A.; Nieger, M.; Airola, K.; Dötz, K. H. Organometallics 1998, 17, 1538.
13. (g) Tomuschat, P.; Kröner, L.; Steckhan, E.; Nieger, M.; Dötz, K. H. Chem. Eur. J. 1999, 5, 700.
14. (h) Weyershausen, B.; Dötz, K. H. Synlett 1999, 231.
15. (i) Ezquerra, J.; Pedregal, C.; Merino, I.; Florez, J.; Barluenga, J.; Garcia-Granda, S.; Llorca, M. A. J. Org. Chem. 1999, 64, 6554.
16. (k) Barluenga, J.; Bernad, P. L.; Concellon, J. M.; Pinera-Nicolas, A.; Garcia-Granda, S. J. Org. Chem. 1997, 62, 6870.
17. (a) Djukic, J. P.; Dötz, K. H.; Pfeffer, M.; De Cian, A.; Fischer, J. Organometallics 1997, 16, 5171.
18. (b) Djukic, J. P.; Maisse, A.; Pfeffer, M.; Dötz, K. H.; Nieger, M. Eur. J. Inorg. Chem. 1998, 1781.
19. (c) Djukic, J. P.; Maisse, A.; Pfeffer M. J. Organomet. Chem. 1998, 567, 65.
20. Djukic, J. P.; Michon, C.; Maisse-François, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064.
21. Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; Wiley: New York, 1994.
22. Solladié-Cavallo, A. Adv. Met.-Org. Chem. 1989, 1, 99.
23. Djukic, J. P.; Maisse, A.; Pfeffer, M.; Dötz, K. H.; Nieger, M. Organometallics 1999, 18, 2786.
24. (a) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21
25. Angew. Chem. 1995, 107, 37.
26. (b) Dorn, R. D.; Baums, D.; Kersten, P.; Regener, R. Adv. Mater. 1992, 4, 464.
27. (c) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291.
28. (d) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1999, 43, 349.
29. (e) Eaton, D. F.; Meredith, G. R.; Miller, J. S. Adv. Mater. 1991, 3, 564.
30. (f) Manners, I. J. Chem. Soc., Chem. Commun. 1999, 857.
31. (g) Kalyanasundaran, K.; Grätzel, M. Coord. Chem. Rev. 1998, 177, 127.
32. (h) Lees, A. J. Coord. Chem. Rev. 1998, 177, 3.
33. (i) Stufkens, D. J.; Vlcek, A. Chem. Rev. 1998, 127.
34. (j) Lees, A. J. Chem. Rev. 1987, 87, 711.
35. (a) Darst, K. P.; Lenhert, P. G.; Lukehart, C. M.; Warfield, L. T. J. Organomet. Chem. 1980, 195, 317.
36. (b) Singh, M. M.; Angelici, R. J. Inorg. Chem. 1984, 23, 2699.
37. (c) Alvarez-Toledano, C.; Parlier, A.; Rudler, M.; Daran, J. C.; Knobler, C.; Jeannin, Y. J. Organomet. Chem. 1987, 328, 357.
38. (d) Miessler, G. L.; Kim, S.; Jacobson, R. A.; Angelici, R. J. Inorg. Chem. 1987, 26, 1690.
39. (e) Casey, C. P.; Nagashima, H. J. Am. Chem. Soc. 1989, 111, 2352.
40. (f) Casey, C. P.; Sakoba, H.; Underiner, T. L. J. Am. Chem. Soc. 1991, 113, 6673.
41. (g) Mashima, K.; Jyodol, K.; Ohyoshi, A.; Takaya, H. Bull. Chem. Soc. Jpn. 1991, 64, 2065.
42. Fedorov, L. A.; Petrovskii, P. V.; Fedin, E. I.; Panosyan, G. A.; Tsoi, A. A.; Baranetskaya, N. K.; Setkina, V. N. J. Organomet. Chem. 1979, 182, 499.
43. (a) Neuse, E. W. J. Organomet. Chem. 1975, 99, 287.
44. (b) Hunter, A. D.; Shilliday, L.; Furey, W. S.; Zaworotko, M. J. Organometallics 1992, 11, 1550.
45. (c) Hunter, A. D.; Mozol, V.; Tsai, S. D. Organometallics 1992, 11, 2251.
46. (d) Djukic, J. P.; Rose-Munch, F.; Rose, E.; Vaissermann, J. Eur. J. Inorg. Chem. 2000, 1295.
47. Ruiz-Morales, Y.; Schreckenbach, G.; Ziegler, T. J. Phys. Chem. 1996, 100, 3359.
48. For leading references please see: (a) Dahl, T. Acta Chem. Scand. 1994, 48, 95.
49. (b) Hunter, C. A. Chem. Soc. Rev. 1994, 101.
50. (c) Müller-Dethlefs, K.; Hobza, P. Chem. Rev. 2000, 100, 143.
51. McGlinchey M. J. Adv. Organomet. Chem. 1992, 34, 285, and references therein.
52. Djukic, J. P.; Pfeffer, M.; Dötz, K. H. C. R. Acad. Sci. Paris, Ser. IIc 1999, 403.
53. (a) Semmelhack, M. F. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 9, p 1117.
54. (b) Nesmeyanov, A. N.; Kolobova, N. E.; Anisimov, K. N.; Markarov, Yu. V. Izv. Akad. Nauk. SSSR, Ser. Khim. 1969, 2665.
55. (c) Fraser, R. R.; Mansour, T. S. J. Organomet. Chem. 1986, 310, C60.
56. (d) Ghavshou, M.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1983, 3065.
57. (e) Semmelhack, M. F.; Bisaha, J.; Czarny, M. J. Am. Chem. Soc. 1979, 101, 768.
58. (f) Card, R. J.; Trahanovski, W. S. J. Org. Chem. 1980, 45, 2560.
59. (g) Uemura, M.; Nishikawa, N.; Take, K.; Ohnishi, M.; Hirotsu, K.; Higushi, T.; Hayashi, Y. J. Org. Chem. 1983, 48, 2349.
60. (h) Rose-Munch, F.; Rose, E. Current Org. Chem. 1999, 3, 445.
61. Oae, S.; Furukawa, N. Adv. Heterocycl. Chem. 1990, 48, 35.
62. (a) Tyler, D. R. Prog. Inorg. Chem. 1988, 36, 125.
63. (b) Brown, T. L. Organometallic Radical Processes, Journal of Organometallic Chemistry Library 32; Trogler, W. C., Ed.; Elsevier: Amsterdam, 1990; p 67.
64. For reviews on organometallic radicals see: (a) Connelly, N. G.; Geiger, W. E. Adv. Organomet. Chem. 1984, 23, 1.
65. (b) Sun, S.; Sweigart, D. Adv. Organomet. Chem. 1996, 40, 171.
66. (a) Ran, S.; Cheng, C. P. J. Chem. Soc., Dalton Trans. 1988, 2695.
67. (b) Milukov, V. A.; Sinyashin, O. G.; Ginzburg, A. G.; Kondratenko, M. A.; Loim, N. M.; Gubskaya, V. P.; Musin, R. Z.; Morozov, V. I.; Batyeva, E. S.; Sokolov, V. I. J. Organomet. Chem. 1995, 493, 221.
68. (c) Mach, K.; Novakova, J.; Raynor, J. B. J. Organomet. Chem. 1992, 439, 341.
69. (d) Symons, M. C. R.; Sweany, R. L. Organometallics 1982, 1, 834.
70. (d) Rattinger, G. B.; Belford, R. L.; Walker, H.; Brown, T. L. Inorg. Chem. 1989, 28, 1059.
71. (e) Myers, R. J. Molecular Magnetism and Magnetic Resonance Spectroscopy; Prentice Hall: London, 1973.
72. (a) Schmaltz, H. G.; Siegel, S.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2383.
73. (b) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
74. (c) Taniguchi, N.; Uemura, M. Synlett 1997, 51.
75. (d) Taniguchi, N.; Uemura, M. Tetrahedron Lett. 1997, 38, 7199.
76. (e) Merlic, C. A.; Walsh, J. C. Tetrahedron Lett. 1998, 39, 2083.
77. (f) Schmaltz, H. G.; Siegel, S.; Bernicke, D. Tetrahedron Lett. 1998, 39, 6683.
78. (g) Schmaltz, H. G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1620.
79. (a) Pfletschinger, A.; Dargel, T. K.; Schmaltz, H. G.; Koch, W. Chem. Eur. J. 1999, 5, 537.
80. (b) Merlic, C. A.; Walsh, J. C.; Tantillo, D. J.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3596.
81. (a) Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction, Evidence, Nature and Consequences, Methods in Stereochemical Analysis; Marchand, A. P., Ed.; Wiley-VCH: New York, 1998.
82. (b) Umezawa, Y.; Tsuboyama, S.; Takahashi, H.; Uzawa, J.; Nishio, M. Tetrahedron 1999, 55, 10047.
83. McCullen, S. B.; Brown, T. L. J. Am. Chem. Soc. 1982, 104, 7496.
84. Ohkita, M.; Lehn, J. M.; Baum, G.; Fenske, D. Chem. Eur. J. 1999, 5, 3471.
85. Katz, T. J. Angew. Chem. Int. Ed. 2000, 39, 1921.
86. Open Mole N. Interactive Structure Solution; Nonius, B. V.: Delft, The Netherlands, 1997.
87. Kündig, E. P.; Ripa, A.; Liu, R.; Amurrio, D.; Bernardinelli, G. Organometallics 1993, 12, 3724.