Nonchelated alkene and alkyne complexes of d0 zirconocene pentafluorophenyl cations

Journal of the American Chemical Society

Volumn 128, Issue 26, 2006, Pages 8638-8650

  Stoebenau III, Edward J ^a   Jordan, Richard F ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE; PHASE EQUILIBRIA; POSITIVE IONS; SUBSTRATES; ZIRCONIUM;

EQUILIBRIUM MIXTURES; METHIDE ABSTRACTION; MULTIPLE BOND; PHCL SOLUTION;

COMPLEXATION;

ALKENE; ALKYNE; ALLYLTRIMETHYLSILANE; CATION; CHLOROBENZENE; COORDINATION COMPOUND; FLUORINE DERIVATIVE; LIGAND; PENTAFLUOROPHENYL CATION; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPARGYLTRIMETHYLSILANE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONOCENE;

ARTICLE; BINDING AFFINITY; CHELATION; CHEMICAL BOND; COMPLEX FORMATION; DISSOCIATION; ENANTIOMER; LOW TEMPERATURE; MOLECULAR INTERACTION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; SURFACE CHARGE;

EID: 33745728185     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057524p     Document Type: Article

References (96)

1. (a) Cossee, P. Tetrahedron Lett. 1960, 17, 12.
2. (b) Cossee, P. J. Catal. 1964, 3, 80.
3. (c) Arlman, E. J.; Cossee, P. J. Catal. 1964, 3, 99.
4. (d) Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
5. (e) Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85.
6. (a) Margl, P.; Deng, L.; Ziegler, T. Top. Catal. 1999, 7, 187.
7. (b) Fan, L.; Harrison, D.; Woo, T. K.; Ziegler, T. Organometallics 1995, 14, 2018.
8. (c) Woo, T. K.; Fan, L.; Ziegler, T. Organometallics 1994, 13, 2252.
9. (d) Lanza, G.; Fragalà, I. L. Top. Catal. 1999, 7, 45.
10. (e) Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
11. (a) Carpentier, J. F.; Wu, Z.; Lee, C. W.; Strömberg, S.; Christopher, J. N.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 7750.
12. (b) Carpentier, J.-F.; Maryin, V. P.; Luci, J.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 898.
13. (c) Wu, Z.; Jordan, R. F.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 5867.
14. Leading references: (a) Casey, C. P.; Klein, J. F.; Pagan, M. A. J. Am. Chem. Soc. 2000, 122, 4320.
15. (b) Casey, C. P.; Carpenetti, D. W., II. Organometallics 2000, 19, 3970.
16. (c) Brandow, C. G.; Mendiratta, A.; Bercaw, J. E. Organometallics 2001, 20, 4253.
17. (d) Casey, C. P.; Carpenetti, D. W., II; Sakurai, H. Organometallics 2001, 20, 4262.
18. (e) Cano, J.; Gómez-Sal, P.; Heinz, G.; Martínez, G.; Royo, P. Inorg. Chim. Acta 2003, 345, 15.
19. (f) Martínez, G.; Royo, P. Organometallics 2005, 24, 4782.
20. (a) Witte, P. T.; Meetsma, A.; Hessen, B.; Budzelaar, P. H. M. J. Am. Chem. Soc. 1997, 119, 10561.
21. (b) Humphries, M. J.; Douthwaite, R. E.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 2000, 2952.
22. (c) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed, Engl. 1992, 31, 1585.
23. (a) Casey, C. P.; Tunge, J. A.; Lee, T.-Y.; Fagan, M. A. J. Am. Chem. Soc. 2003, 125, 2641.
24. (b) Casey, C. P.; Lee, T.-Y.; Tunge, J. A.; Carpenetti, D. W., II. J. Am. Chem. Soc. 2001, 123, 10762.
25. (a) Bonazza, A.; Cumurati, I.; Guidotti, S.; Mascellari, N.; Resconi, L. Macromol. Chem. Phys. 2004, 205, 319.
26. (b) For related species see: Kehr, G.; Fröhlich, R.; Wibbeling, B.; Erker, G. Chem. Eur. J. 2000, 6, 258.
27. Preliminary communication: Stoebenau, E. J., III; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 11170.
28. 0 compounds, see: (a) Chambers, R. D.; Chivers, T. Organomet. Chem. Rev. 1966, 1, 279.
29. (b) Alonso, P. J.; Favello, L. R.; Forniés, J.; García-Monforte, M. A.; Menjón, B. Angew. Chem., Int. Ed. 2004, 43, 5225.
30. (c) Deacon, G. B.; Forsyth, C. M. Organometallics 2003, 22, 1349.
31. (d) Hauber, S.-O.; Lissner, F.; Deacon, G. B.; Niemeyer, M. Angew. Chem., Int. Ed. 2005, 44, 5871.
32. (e) Hauber, S.-O.; Lissner, F.; Deacon, G. B.; Niemeyer, M. Angew. Chem., Int. Ed. 2005, 44, 5871.
33. (f) Maron, L.; Werkema, E. L.; Perrin, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2005, 127, 279.
34. 5 species, see: (g) Ara, I.; Forniés, J.; García-Monforte, M. A.; Martín, A.; Menjón, B. Chem. Eur. J. 2004, 10, 4186.
35. (a) Dioumaev, V. K.; Harrod, J. F. Organometallics 1997, 16, 2798.
36. (b) Chaudhari, M. A.; Stone, F. G. A. J. Chem. Soc. A 1966, 838.
37. (c) Coe, P. L.; Stephens, R.; Tatlow, J. C. J. Chem. Soc. 1962, 3227.
38. Bochmann, M.; Sarsfield, M. J. Organometallics 1998, 17, 5908.
39. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391 and references therein.
40. 2(μ-O) see: Marsella, J. A.; Folting, K.; Huffman, J. C.; Caulton, K. G. J. Am. Chem. Soc. 1981, 103, 5596.
41. Hillhouse, G. L.; Bercaw, J. E. J. Am. Chem. Soc. 1984, 106, 5472.
42. - abstracting agent, see: Forniés, J.; Martín, A.; Martín, L. F.; Menjón, B.; Tsipis, A. Organometallics 2005, 24, 3539.
43. Korolev, A. V.; Ihara, E.; Guzei, I. A.; Young, V. G., Jr.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 8291.
44. Wieser, U.; Babushkin, D.; Brintzinger, H.-H. Organometallics 2002, 21, 920.
45. (a) Pindado, G. J.; Lancaster, S. J.; Thornton-Pett, M.; Bochmann, M. J. Am. Chem. Soc. 1998, 120, 6816.
46. (b) Kraft, B. M.; Jones, W. D. J. Organomet. Chem. 2002, 658, 132.
47. Edelbach, E. L.; Rahman, A. K. F.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 3170.
48. (a) Wu, F.; Dash, A. K.; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 15360.
49. (b) Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem., Int. Ed. Engl. 1990, 29, 780.
50. Leblanc, J. C.; Moïse, C. Org. Magn. Reson. 1980, 14, 157.
51. 2. Stoebenau, E. J., III; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 3222.
52. 5 ring (vida infra).
53. Blackwell, J. M.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 1295.
54. (a) Müller, T.; Juhasz, M.; Reed, C. A. Angew. Chem, Int. Ed. 2004, 43, 1543.
55. (b) Müller, T.; Meyer, R.; Lennartz, D.; Siehl, H.-U. Angew. Chem., Int. Ed. 2000, 39, 3074.
56. (c) Koch, E.-W.; Siehl, H.-U.; Hanack, M. Tetrahedron Lett. 1985, 26, 1493.
57. (d) Siehl, H.-U.; Kaufmann, F.-P.; Apeloig, Y.; Braude, V.; Danovich, D.; Berndt, A.; Stamatis, N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1479.
58. (e) Müller, T.; Margraf, D.; Syha, Y. J. Am. Chem. Soc. 2005, 127, 10852.
59. 5Cl] ≈ 4.5 eu.
60. trans and p-F resonances of 7a showed no trend with temperature and averaged 1.2 Hz between -38 and +2 °C.
61. (a) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935.
62. (b) Johnston, E. R.; Dellwo, M. J.; Hendrix, J. J. Magn. Reson. 1986, 66, 399.
63. (c) Perrin, C. L.; Gipe, R. K. J. Am. Chem. Soc. 1984, 106, 4036.
64. 7a.
65. The nomenclature of this process is from: Prosenc, M.-H.; Brintzinger, H.-H. Organometallics 1997, 16, 3889.
66. trans of 7a.
67. 1H NMR Cp resonances of 7a.
68. Peng, T.-S.; Gladysz, J. A. J. Am. Chem. Soc. 1992, 114, 4174.
69. 5 insertion would exchange the Cp rings (due to site epimerization in the insertion products), it does not exchange the allylic hydrogens. In addition, the insertion products would be more reactive towards insertion than 4a itself, and ATMS polymerization would be observed, which is not the case.
70. 33 and involving, for example, oxidative addition or M-carbene formation, are not reasonably possible for 7a,b.
71. (a) Matchett, S. A.; Zhang, G.; Frattarelli, D. Organometallics 2004, 23, 5440.
72. (b) Chang, T. C. T.; Foxman, B. M.; Rosenblum, M.; Stockman, C. J. Am. Chem. Soc. 1981, 103, 7361.
73. Enantioface exchange in 7a,b by dissociation of into 4a,b and ATMS followed by recombination within a solvent cage, with slower diffusion of ATMS out of the cage, cannot be definitively excluded.
74. (a) Sillars, D. R.; Landis, C. R. J. Am. Chem. Soc. 2003, 125, 9894.
75. (b) Yoder, J. C.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 2548.
76. (c) Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1996, 118, 9024.
77. (d) Kelly, W. M.; Wang, S.; Collins, S. Macromolecules 1997, 30, 3151.
78. Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M.-Y.; Jung, I. N. Organometallics 1995, 14, 2361.
79. Schade, C.; Mayr, H. Makromol. Chem., Rapid Commun. 1988, 9, 477.
80. (a) Horton, A. D. Chem. Commun. 1992, 185.
81. (b) Akita, M.; Yasuda, H.; Nakamura, A. Bull. Chem. Soc. Jpn. 1984, 57, 480.
82. (c) den Haan, K. H.; Wielstra, Y.; Teuben, J. H. Organometallics 1987, 6, 2053.
83. (d) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980.
84. Zirconocene catalysts polymerize ATMS by the same coordination/insertion mechanism as for other olefins, and exhibit the same metallocene-symmetry/ polymer-tacticity relationships. (a) Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025.
85. (b) Habaue, S.; Baraki, H.; Okamoto, Y. Macromol. Chem. Phys. 1998, 199, 2211.
86. (c) Natta, G.; Mazzanti, G.; Longi, P.; Bernardini, F. J. Polym. Sci. 1958, 31, 181.
87. Liu, Z.; Somsook, E.; White, C. B.; Rosaaen, K. A.; Landis, C. R. J. Am. Chem. Soc. 2001, 123, 11193.
88. Tjaden, E. B.; Swenson, D. J.; Jordan, R. F.; Petersen, J. L. Organometallics 1995, 14, 371.
89. Samuel, E.; Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263.
90. Couturier, S.; Tainturier, G.; Gautheron, B. J. Organomet. Chem. 1980, 195, 291.
91. Van Geet, A. L. Anal. Chem. 1970, 42, 679.
92. Trace amounts (1-3%) of 6a were observed in some samples of 4a. Compound 6a is formed at the beginning of the reaction and does not grow in at longer reaction times. 6a is probably formed by the reaction of 4a with alkyl chloride impurities in the solvent or trityl salt, or from Zr-Cl impurities in 3a.
93. +, analogous to 6a.
94. Minitab, v. 11.2; Minitab Inc.: State College, PA, 1996.
95. gNMR, v. 4.1.2; Adept Scientific: Letchworth, UK, 2000.
96. MATLAB, v. 5.0.0.4073; The Math Works, Inc.: Natick, MA, 1996.