Responsive iron neighboring group participation in amino-substituent-stabilized [3]ferrocenophane α-carbenium ions: A combined theoretical and experimental study

Organometallics

Volumn 23, Issue 1, 2004, Pages 21-25

  Liptau, Patrick ^a   Neumann, Markus ^a   Erker, Gerhard ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Grimme, Stefan ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; COPOLYMERIZATION; IRON COMPOUNDS; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS; X RAY CRYSTALLOGRAPHY;

ABSTRACTION; CARBENIUM IONS; DENSITY FUNCTIONAL THEORY; FERROCENOPHANE;

ORGANOMETALLICS;

EID: 1642578085     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034214b     Document Type: Article

References (49)

1. Togni, A., Hayashi, T., Eds. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, 1995.
2. Togni, A., Haltermann, R. L., Eds. In Metallocenes: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 1998
3. Josiphos: Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
4. Mernyi, A.; Kratky, C.; Weissensteiner, W.; Widhalm, M. J. Organomet. Chem. 1996, 508, 209-218.
5. Gómez-de la Torre, F.; Jalón, F. A.; López-Agenjo, A.; Manzano, B. R.; Rodríguez, A.; Sturm, T.; Weissensteiner, W.; Martínez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
6. Jalón, F. A.; López-Agenjo, A.; Manzano, B. R.; Moreno-Lara, M.; Rodríguez, A.; Sturm, T.; Weissensteiner, W. J. Chem. Soc., Dalton Trans. 1999, 4031-4039.
7. Sturm, T.; Weissensteiner, W.; Mereiter, K.; Kégl, T.; Jeges, G.; Petölz, G.; Kollár, L. J. Organomet. Chem. 2000, 595, 93-101.
8. Weissenbach, M.; Sturm, T.; Kalchhauser, K.; Kratky, C.; Weissensteiner, W. Monatsh. Chem. 2002, 133, 991-1009.
9. Liptau, P.; Seki, T.; Kehr, G.; Abele, A.; Fröhlich, R.; Erker, G.; Grimme, S. Organometallics 2003, 22, 2226-2232.
10. (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393.
11. Gokel, G.; Marquarding, D.; Ugi, I. J. Org. Chem. 1972, 37, 3052-3058.
12. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151.
13. (b) Watts, W. E. J. Organomet. Chem. Library 1979, 7, 399-459.
14. Pearson, A. J. Metallo-Organic Chemistry; Wiley: New York, 1985; p 319-322.
15. (c) Theoretical work: Gleiter, R.; Seeger, R. Helv. Chim. Acta 1971, 54, 1217-1220.
16. Gleiter, R.; Seeger, R.; Binder, H.; Fluck, E.; Cais, M. Angew. Chem. 1972, 84, 1107-1109.
17. Angew. Chem., Int. Ed. Engl. 1972, 11, 1028-1030.
18. Gleiter, R.; Schimanke, H.; Silverio, S. J.; Büchner, M.; Huttner, G. Organometallics 1996, 15, 5635-5640.
19. Volland, M. A. O.; Kudis, S.; Helmchen, G.; Hyla-Kryspin, I.; Rominger, F.; Gleiter, R. Organometallics 2001, 20, 227-230.
20. Caynela, E. M.; Xiao, L.; Sturm, T.; Manzano, B. R.; Jalón, F. A.; Weissensteiner, W. Tetrahedron: Asymmetry 2000, 11, 861-869.
21. Manzano, B. R.; Jalón, F. A.; Gómez-de la Torre, F.; López-Agenjo, A. M.; Rodríguez, A. M.; Mereiter, K.; Weissensteiner, W.; Sturm, T. Organometallics 2002, 21, 789-802.
22. Sturm, T.; Weissensteiner, W.; Spindler, F.; Mereiter, K.; López-Agenjo, A. M.; Manzano, B. R.; Jalón, F. A. Organometallics 2000, 21, 1766-1774, and references therein.
23. Tainturier, G.; Chhor y Sok, K.; Gautheron, B. C. R. Acad. Sci. Paris C 1973, 1269-1270.
24. Chhor y Sok, K.; Tainturier, G.; Gautheron, B. Tetrahedron Lett. 1974, 25, 2207-2208.
25. Chhor y Sok, K.; Tainturier, G.; Gautheron, B. J. Organomet. Chem. 1977, 132, 173-189.
26. Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R., Erker, G. J. Organomet. Chem. 2001, 637, 621-630.
27. Liptau, P.; Tebben, L.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2003, in press.
28. Watanabe, M.; Motoyama, I.; Takayama, T. J. Organomet. Chem. 1996, 524, 9-18.
29. Kupfer, V.; Thewalt, U.; Tišlerová, I.; Štěpnička, P.; Gyepes, R.; Kubišta, J.; Horáček, M.; Mach, K. J. Organomet. Chem. 2001, 620, 39-50.
30. Harrington, L. E.; Vargas-Baca, I.; Reginato, N.; McGlinchey, M. J. Organometallics 2003, 22, 663-339, and references therein.
31. Williams, G. H.; Traficante, D. F.; Seyferth, D. J. Organomet. Chem. 1973, 60, C53-C56.
32. This effect was recently used effectively in Lewis acid borane chemistry: Kehr, G.; Fröhlich, R.; Wibbeling, B.; Erker, G. Chem. Eur. J. 2000, 6, 258-266.
33. Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 1999, 586, 218-222
34. 2000, 595, 307-312.
35. Knüppel, S.; Erker, G.; Fröhlich, R. Angew. Chem. 1999, 111, 2048-2051
36. Angew. Chem., Int. Ed. 1999, 38, 1923-1926.
37. Bai, S. D.; Wei, X.-H.; Guo, J.-P.; Liu, D.-S.; Zhou, Z.-Y. Angew. Chem. 1999, 111, 2051-2054
38. Angew. Chem., Int. Ed. 1999, 38, 1926-1928.
39. Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc. London 1963, 212.
40. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
41. Massey, A. G.; Park, A. J. Organometallic Syntheses; King, R. B., Eisch, J. J., Eds.; Elsevier: New York, 1986; Vol. 3, p 461.
42. Blaschke, U.; Erker, G.; Nissinen, M.; Wegelius, E.; Fröhlich, R. Organometallics 1999, 18, 1224-1234.
43. Blaschke, U.; Menges, F.; Erker, G.; Fröhlich, R. Eur. J. Inorg. Chem. 1999, 621-632.
44. (a) Ahlrichs, R.; Bär, M.; Baron, H.-P.; Bauernschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Haase, F.; Häser, M.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A.; Schneider, U.; Treutler, O.; von Arnim, M.; Weigend, F.; Weis, P.; Weiss, H. TURBOMOLE (Vers. 5.5); Univesität Karlsruhe, 2002.
45. (b) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
46. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
47. (c) Scḧfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577.
48. (d) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283-289.
49. (e) All basis sets are available from the TURBOMOLE homepage, http://www.turbomole.com. via FTP server button (in the subdirectories basen (AO basis sets) and jbasen (RI basis sets)).