Anodic electrochemistry of multiferrocenyl phosphine and phosphine chalcogenide complexes in weakly nucleophilic electrolytes

Organometallics

Volumn 24, Issue 1, 2005, Pages 48-52

  Barrière, Frédéric ^a,c   Kirss, Rein U ^b   Geiger, William E ^a  

^a UNIVERSITY OF VERMONT   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

^c UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANODIC ELECTROCHEMISTRY; NUCLEOPHILIC ELECTROLYTES; ONE-ELECTRON OXIDATION;

ADSORPTION; CHARGE TRANSFER; DIMERIZATION; ELECTROLYTES; NEGATIVE IONS; OXIDATION; REACTION KINETICS;

ELECTROCHEMISTRY;

EID: 12444308312     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040123i     Document Type: Article

References (41)

1. Leading references in: (a) Ihara, T.; Nakayama, M.; Murata, M.; Nakano, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1997, 1609. (b) Horie, M.; Sakano, T.; Osakada, K.; Nakao, H. Organometallics 2004, 23, 18. (c) Patolsky, F.; Weizmann, Y.; Wilner, I. J. Am. Chem. Soc. 2002, 124, 770. (b) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856.
2. Leading references in: (a) Ihara, T.; Nakayama, M.; Murata, M.; Nakano, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1997, 1609. (b) Horie, M.; Sakano, T.; Osakada, K.; Nakao, H. Organometallics 2004, 23, 18. (c) Patolsky, F.; Weizmann, Y.; Wilner, I. J. Am. Chem. Soc. 2002, 124, 770. (b) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856.
3. Leading references in: (a) Ihara, T.; Nakayama, M.; Murata, M.; Nakano, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1997, 1609. (b) Horie, M.; Sakano, T.; Osakada, K.; Nakao, H. Organometallics 2004, 23, 18. (c) Patolsky, F.; Weizmann, Y.; Wilner, I. J. Am. Chem. Soc. 2002, 124, 770. (b) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856.
4. Leading references in: (a) Ihara, T.; Nakayama, M.; Murata, M.; Nakano, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1997, 1609. (b) Horie, M.; Sakano, T.; Osakada, K.; Nakao, H. Organometallics 2004, 23, 18. (c) Patolsky, F.; Weizmann, Y.; Wilner, I. J. Am. Chem. Soc. 2002, 124, 770. (b) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856.
5. Leading references to ferrocenes having Lewis-base substituents: (a) Herberhold, M. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1996; Chapter 5. (b) Arjun, M.; Barlow, S.; Day, M. W.; Marder, S. R. Organometallict 1999, 18, 454. (c) Shafir, A.; Power, M. P.; Whitener, G. D.; Arnold, J. Organometallics 2000, 19, 3978.
6. Leading references to ferrocenes having Lewis-base substituents: (a) Herberhold, M. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1996; Chapter 5. (b) Arjun, M.; Barlow, S.; Day, M. W.; Marder, S. R. Organometallict 1999, 18, 454. (c) Shafir, A.; Power, M. P.; Whitener, G. D.; Arnold, J. Organometallics 2000, 19, 3978.
7. Leading references to ferrocenes having Lewis-base substituents: (a) Herberhold, M. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1996; Chapter 5. (b) Arjun, M.; Barlow, S.; Day, M. W.; Marder, S. R. Organometallict 1999, 18, 454. (c) Shafir, A.; Power, M. P.; Whitener, G. D.; Arnold, J. Organometallics 2000, 19, 3978.
8. (a) Kotz, J. C.; Nivert, C. L. J. Organomet. Chem. 1973, 52, 387.
9. (b) Kotz, J. C.; Nivert, C. L.; Lieber, J. M. J. Organomet. Chem. 1975, 91, 87.
10. Gref, A.; Diter, P.; Guillaneux, D.; Kagan, H. B. New J. Chem. 1997, 21, 1353.
11. Durfey, D. A.; Kirss, R. U.; Frommen, C. Reiff, W. M. Inorg. Chim. Acta 2004, 357, 311.
12. Britton, W. E.; Kashyap, R.; El-Hashash, M.; El-Kady, M.; Herberhold, M. Organometallics 1986, 5, 1029.
13. Houlton, A.; Bishop, P. T.; Roberts, R. M. G.; Silver, R. J.; Herberhold, M. J. Organomet. Chem. 1989, 364, 381.
14. Butler, I. R.; Griesbach, U.; Zanello, R; Fontani, M.; Hibbs, D.; Hursthouse, M. B.; Abdul Malik, K. L. M. J. Organomet. Chem. 1996, 565, 243.
15. LeSuer, R. J.; Geiger, W. E. Angew. Chem., Int. Ed. 2000, 39, 248.
16. Camire, N.; Nafady, A.; Geiger, W. E. J. Am. Chem. Soc. 2002, 124, 7260.
17. Barrière, F.; Camire, N.; Geiger, W. E.; Mueller-Westerhoff, U. T.; Sanders, R. J. Am. Chem. Soc. 2002, 124, 7262.
18. Barrière, F.; LeSuer, R. J.; Geiger, W. E. In New Trends in Molecular Electrochemistry; Pombeiro, A. J. L., Amatore, C., Eds.; FontisMedia: Lausanne, Switzerland, 2004, pp 413-444.
19. Camire, N.; MueUer-Westerhoff, U. T.; Geiger, W. E. J. Organomet. Chem. 2001, 637-639, 823.
20. Durfey, D. A.; Kirss, R. U.; Frommen, C.; Feighery, W. Inorg. Chem. 2000, 39, 3506.
21. Downard, A. J.; Goodwin, N. J.; Henderson, W. J. Organomet. Chem. 2003, 676, 62.
22. (a) Gan, K.-S.; Hor, T. S. A. In ref 2a, Chapter 1.
23. (b) Cullen, W. R.; Woolins, J. D. Coord. Chem. Rev. 1981, 39, 1.
24. Miller, T. M.; Ahmed, K. J.; Wrighton, M. Inorg. Chem, 1989, 28, 2347.
25. (a) Corain, B.; Longato, B.; Favero, G.; Ajó, Pilloni, G.; Russo, U.; Kreissl, F. R. Inorg. Chim. Acta 1989, 157, 259.
26. (b) Pilloni, G.; Longato, B.; Corain, B. J. Organomet. Chem. 1991, 420, 57.
27. Nataro, C.; Campbell, A. N.; Ferguson, M. A.; Incarvito, C. D.; Rheingold, A. L. J. Organomet. Chem. 2003, 673, 47.
28. Foucher, D. A.; Honeyman, C. H.; Nelson, J. M.; Tang, B. Z.; Manners, I. Angew. Chem., Int. Ed. Engl. 1993, 32, 1709.
29. Sollott, G. P.; Mertwoy, H. E.; Portnoy, S.; Snead, J. L. J. Org. Chem. 1963, 28, 1900.
30. Sollott, G. P.; Petersen, Jr., W. R. J. Organomet. Chem. 1966, 4, 491.
31. LeSuer, R. J.; Geiger, W. E. Anal. Chem. 2004, 76, 6395.
32. Gritzner, G.; Kuta, J. Pure Appl. Chem. 1984, 56, 461.
33. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
34. Geiger, W. E. In Laboratory Techniques in Electroanalytical Chemistry, 2nd ed.; Kissinger, P. T., Heineman, W. R., Eds.; Marcel Dekker: New York, 1996; Chapter 23.
35. (a) Culcasi, M.; Berchadsky, Y.; Gronchi, G.; Tordo, P. J. Org. Chem. 1991, 56, 3537.
36. (b) Toshikatsu, T.; Abe, A.; Suda, K; Ohmori, H. J. Chem. Soc., Chem. Commun. 1990, 1310.
37. (c) Kargin, Yu.; Nikitin, E. V.; Parakin, O. V.; Romanov, G. V.; Pudovik, A. N. Dokl. Akad. Nauk SSSR 1978, 241, 131; Chem. Abstr. 1978, 59, 119655.
38. (c) Kargin, Yu.; Nikitin, E. V.; Parakin, O. V.; Romanov, G. V.; Pudovik, A. N. Dokl. Akad. Nauk SSSR 1978, 241, 131; Chem. Abstr. 1978, 59, 119655.
39. (d) Kargin, Yu.; Nikitin, E. V.; Parakin, O. V.; Mironov, B. S.; Pudovik, A. N. Dokl. Akad. Nauk SSSR 1976, 226, 1101.
40. -1 is characteristic of ferrocenium cations. Similar features are seen in [6][DDQ], as described in ref 14.
41. Liotta, D., Ed. Organoselenium Chemistry; Wiley: New York, 1987.