Ion-pair structure as a determinant of solvent dependence. Solvent-selective formation of tert-butylbis(indenyl)phosphine and tert-butyl(n-butyl)indenylphosphine

Organometallics

Volumn 21, Issue 14, 2002, Pages 2898-2904

  Malefetse, Tshepo J ^a   Swiegers, Gerhard F ^b   Coville, Neil J ^a   Fernandes, Manuel A ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ORGANIC SOLVENTS; PRECIPITATION (CHEMICAL); SYNTHESIS (CHEMICAL); TOLUENE;

CHIRAL INTERMEDIATES;

ORGANOMETALLICS;

EID: 0038392401     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010736k     Document Type: Article

References (44)

1. For example: (a) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1999, 583, 11.
2. (b) Licht, E. H.; Alt, H. G.; Milius, W.; Abu-Orabi, S. J. Organomet. Chem. 1998, 560, 69.
3. (c) Steinhorst, A.; Erker, G.; Grehl, M.; Frölich, R. J. Organomet. Chem. 1997, 542, 191.
4. (d) Ready, T. E.; Chien, J. C. W.; Rausch, M. D. J. Organomet. Chem. 1996, 519, 21.
5. (e) Meurling, L. Acta Chem. Scand. B 1974, 28, 295.
6. (f) Gridnev, I.; Meller, A. Main Group Met. Chem. 1998, 21, 271.
7. For example: (a) Knizek, J.; Krossing, I.; Nöth, H.; Ponikwar, W. Eur. J. Inorg. Chem. 1998, 505.
8. (b) Ashe, A. J., III; Fang, X.; Kampf, J. W. Organometallics 1999, 18, 2288.
9. (c) Barday, E.; Frange, B.; Hanquet, B.; Herberich, G. E. J. Organomet. Chem. 1999, 572, 225.
10. (d) Herberich, G. E.; Barday, E.; Fischer, A. J. Organomet. Chem. 1998, 567, 127.
11. (e) Braunschweig, H.; von Koblinski, C.; Neugebauer, M.; Englert, U.; Zheng, X. J. Organomet. Chem. 2001, 619, 305.
12. For example: (a) Schumann, H.; Karasiak, D. K.; Muhle, S. H.; Halterman, R. L.; Kaminsky, W.; Weingarten, U. J. Organomet. Chem. 1999, 579, 356.
13. (b) Kerber, R. C.; Hodos, M. A. J. Org. Chem. 1968, 33, 1169.
14. (c) Melera, A.; Claesen, M.; Vandergaege, H. J. Org. Chem. 1964, 29, 3705.
15. (a) Elschenbroich, C.; Salzer, A. Organometallics, 2nd ed.; Weinheim: 1992; p 20 and p 24, and references therein.
16. (b) Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: Oxford, 1974; p 8, and references therein.
17. (c) Haiduc, I.; Zuckerman, J. J. Basic Organometallic Chemistry; Walter de Gruyer: Berlin, 1985; p 48, and references therein.
18. Cox, R. H.; Terry, H. W.; Harrison, L. W. J. Am. Chem. Soc. 1971, 93, 3297.
19. Vos, H. W.; Blom, H. H.; Velthorst, N. H.; MacLean, C. J. Chem. Soc., Perkin Trans. 2 1972, 635, and references therein.
20. Cox, H. H.; Terry, H. W., Jr. J. Magn. Reson. 1974, 14, 317.
21. Streitwieser, A., Jr.; Chang, C. J.; Hollyhead, W. B.; Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 5288.
22. 13C NMR, e.g.: (a) Edlund, U. Org. Magn. Reson. 1979, 12, 661.
23. (b) Eliasson, B.; Johnels, D.; Wold, S.; Edlund, U. Acta Chem. Scand. B 1982, 36, 155, and references therein.
24. (c) Lejon, T.; Edlund, U. Acta Chem. Scand. 1989, 43, 275.
25. 1H NMR, e.g.: Gooijer, C.; Veithorst, N. H. Org. Magn. Reson. 1979, 12, 684.
26. The structure of indenyllithium ion pairs/aggregates in solution can be studied using fluorescence spectroscopy, e.g.: Vos, H. W.; MacLean, C.; Veithorst, N. H. J. Chem. Soc., Faraday Trans. 2 1976, 72, 63.
27. The structure of indenyllithium ion pairs/aggregates in solution can be studied using combinations of the techniques described in refs 9-11, for example: Edlund, U.; Eliasson, B.; Kowalewski, J.; Trogen, L. J. Chem. Soc., Perkin Trans. 2 1981, 1260.
28. Fallis, K. A.; Anderson, G. K.; Rath, N. P. Organometallic 1992, 11, 885.
29. Lensink, C.; Gainsford, G. J. Aust. J. Chem. 1998, 51, 667.
30. Schaverien, C. J.; Ernst, R.; Terlouw, W.; Schut, P.; Sudmeijer, O.; Budzelaar, P. H. M. J. Mol. Catal. A 1998, 128, 245.
31. Other P-bridged ansa-metallocene group IV complexes have also been reported. For example: (a) Shin, J. H.; Hascall, T.; Parkin, G. Organometallics 1999, 18, 6.
32. (b) Leyser, N.; Schmidt, K.; Brintzinger, H.-H. Organometallics 1998, 17, 2155.
33. Phospholyl rings have also been employed in ansa-zirconocene olefin polymerization catalysts, e.g.: (c) Janiak, C.; Lange, K. C. H.; Versteeg, U.; Lenz, D.; Budzelaar, P. H. M. Chem. Ber. 1996, 129, 1517.
34. (d) de Boer, E. J. M.; Gilmore, I. J.; Korndorffer, F. M.; Horton, A. D.; van der Linden, A.; Royan, B. W.; Ruisch, B. J.; Schoon, L.; Shaw, R. W. J. Mol. Catal. A Chem. 1998, 128, 155.
35. Fild, M.; Stelzer, O.; Schmutzler, R.; Doak, G. O. Inorganic Syntheses; Wiley: New York. 19XX; Vol. XIV, p 4.
36. Perrin, D. D.; Armarego, W. L. F. Purification of Organic Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
37. SAINT+, version 6.02 (includes XPREP and SADABS); Bruker AXS Inc.: Madison, WI, 1999.
38. Sheldrick, G. M. SADABS; University of Göttingen: Germany, 1996.
39. SHELXTL, version 5.1. (includes XS, XL, XP, XSHELL); Bruker AXS Inc.: Madison, WI, 1999.
40. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
41. AB used in: Dogan, J.; Schulte, J. B.; Swiegers, G. F.; Wild, S. B. J. Org. Chem. 2000, 65, 951. Correction: J. Org. Chem, 2000, 65, 4782.
42. Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5301.
43. Rufanov, K.; Avtomonov, E.; Kazennova, N.; Kotov, V.; Khvorost, A.; Lemenovskii, D.; Lorbeth, J. J. Organomet. Chem. 1997, 536-537, 361.
44. The mechanism of base-catalyzed prototropic indene isomerizations of this type is known: Almy, J.; Uyeda, R. T.; Cram, D. J. J. Am. Chem. Soc. 1967, 89, 6768, and references therein.