Synthesis, structure, and electrochemistry of an electron-rich chiral diaminoferrocene, (S,S)-Bis(2,5-dimethylpyrrolidinyl)ferrocene

Organometallics

Volumn 24, Issue 21, 2005, Pages 5184-5187

  Blank, Natalia F ^a   Glueck, David S ^a   Zakharov, Lev N ^b   Rheingold, Arnold L ^b   Saybolt, Matthew D ^c   Ghent, Brenna L ^c   Nataro, Chip ^c  

^a Dartmouth College   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c LAFAYETTE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL; DIAMINOFERROCENE; PLANAR NITROGEN; REDOX POTENTIAL;

CHEMICAL BONDS; CRYSTAL STRUCTURE; ELECTROCHEMICAL CORROSION; ELECTRONS; NITROGEN; NITROGEN COMPOUNDS; REACTION KINETICS; SULFUR COMPOUNDS;

ORGANOMETALLICS;

EID: 27144536662     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050367i     Document Type: Article

References (28)

1. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
2. Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372.
3. Nakayama, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 9735-9750.
4. Illesinghe, J.; Ebeling, R.; Ferguson, B.; Patel, J.; Campi, E. M.; Jackson, W. R.; Robinson, A. J. Aust. J. Chem. 2004, 57, 167-176.
5. Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363-9366.
6. Togni, A.; Hayashi, T. Ferrocenes. Homogeneous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995.
7. Cahill, J. P.; Bohnen, F. M.; Goddard, R.; Kruger, C.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 3831-3839.
8. As in the chiral phosphine literature (for example, Josiphos), we call 6 "Natamine" after Natalia Blank, who proposed and carried out its synthesis.
9. Shafir, A.; Power, M. P.; Whitener, G. D.; Arnold, J. Organometallics 2000, 19, 3978-3982.
10. Carre, F.; Guerin, C.; Henner, B. J. L.; Uerpmann, C. J. Organomet. Chem. 2002, 654, 210-215.
11. Wrackmeyer, B.; Klimkina, E. V.; Milius, W. Inorg. Chem. Commun. 2004, 7, 412-416.
12. Inyushin, S.; Shafir, A.; Sheats, J. E.; Minihane, M.; Whitten, C. E., Jr.; Arnold, J. Polyhedron 2004, 23, 2937-2942.
13. Naberfeld, G. Ph.D. Thesis, Ruhr-Universitat Bochum, Mulheim an der Ruhr, 2000.
14. (a) See ref 11.
15. (b) Wrackmeyer, B.; Klimkina, E. V.; Milius, W. Struct. Chem. 2004, 15, 333-337.
16. (c) Wrackmeyer, B.; Klimkina, E. V.; Milius, W. Inorg. Chem. Commun. 2004, 7, 884-888.
17. Ohwada, T.; Hiaro, H.; Ogawa, A. J. Org. Chem. 2004, 69, 7486-7494.
18. As noted by a reviewer, even shorter C-N and longer Fe-C(N) bonds were observed in the 1,1′-diaminoferrocenium cation (entry 5, Table 2), consistent with contribution from a resonance structure analogous to 6′, where Cp-to-Fe donation is favored by the positive charge at the metal center.
19. Ramachandran, B. M.; Trupia, S. M.; Geiger, W. E.; Carroll, P. J.; Sneddon, L. G. Organometallics 2002, 21, 5078-5090.
20. Britton, W. E.; Kashyap, R.; El-Hashash, M.; El-Kady, M.; Herberhold, M. Organometallics 1986, 5, 1029-1031.
21. Siemeling, U.; Kuhnert, O.; Neumann, B.; Stammler, A.; Stammler, H.-G.; Bildstein, B.; Malaun, M.; Zanello, P. Eur. J. Inorg. Chem. 2001, 913-916.
22. Stahl, K.-P.; Boche, G.; Massa, W. J. Organomet. Chem. 1984, 277, 113-125
23. Shafir, A.; Power, M. P.; Whitener, G. D.; Arnold, J. Organometallics 2001, 20, 1365-1369.
24. Rayn, M. F.; Richardson, D. E.; Lichtenberger, D. L.; Gruhn, N. E. Organometallics 1994, 13, 1190-1199.
25. Lu, S.; Strelets, V. V.; Ryan, M. F.; Pietro, W. J.; Lever, A. B. P. Inorg. Chem. 1996, 35, 1013-1023.
26. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
27. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
28. LeSuer, R.; Geiger, W. E. Angew. Chem., Int. Ed. 2000, 39, 248-250.