Synthesis, structure, and reactivity of (C5H4SiMe3)2Y{(μ-FC 6F4)(μ-Me)B(C6F5)2}: Tight ion pairing in a cationic lanthanide complex

Organometallics

Volumn 17, Issue 6, 1998, Pages 1004-1006

  Song, Xuejing ^a   Thornton Pett, Mark ^a   Bochmann, Manfred ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000942170     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971044s     Document Type: Article

References (51)

1. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
2. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
3. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
4. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
5. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
6. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
7. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
8. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
9. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
10. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
11. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
12. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
13. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
14. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
15. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
16. Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 4, p 11. For recent examples of catalytic reactions, see also: (a) Heeres, H. J.; Teuben, J. H. Organometallics 1991, 10, 1980. (b) Deelman, B. J.; Bijpost, E. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1995, 1741. (c) Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291. (d) Schaverien, C. J. J. Chem. Soc., Chem. Commun. 1992, 11. (e) Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606. (f) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045. (g) Yasuda, H.; Ihara, E. Macromol. Chem. Phys. 1995, 196, 2417. (h) Yasuda, H.; Ihara, E. Tetrahedron 1995, 51, 4563. (i) Ihara, E.; Nodono, M.; Yasuda, H.; Kanehisa, N.; Kai, Y. Macromol. Chem. Phys. 1996, 197, 1909. (j) Yang, X. M.; Seyam, A. M.; Fu, P. F.; Marks, T. J. Macromolecules 1994, 27, 4625. (k) Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276. (l) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705. (m) Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366. (n) Boffa, L. S.; Novak, B. M. Macromolecules 1997, 30, 3494. (o) Evans, W. J.; De Coster, D. M.; Greaves, J. Macromolecules 1995, 28, 7929.
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28. 2Y: C, 47.20 (46.75); H, 3.26 (3.30); F, 32.03 (31.65).
29. 8, 25°C): δ -133.4 (br, 6 F, o-F), -160.4 (br, 3 F, p-F), -165.3 (br, 6 F, m-F).
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35. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
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38. 4SSi: C, 55.53; H, 6.21. Found: C, 55.91; H, 6.39.
39. 6 solution.
40. pc = cathodic peak potential.
41. For a discussion of electrode reactions with coupled homogeneous chemical reactions, see: Bard, A. J.; Faulkner, L. R. Electrochemical Methods; Wiley: New York, 1980; pp 429-483.
42. 19 The least amount of adsorption was observed when either a glassy-carbon or platinum electrode was used in acetonitrile solution.
43. For a discussion of adsorption in cyclic voltammetry experiments, see: Bard, A. J.; Faulkner, L. R. Electrochemical Methods; Wiley: New York, 1980; pp 525-532.
44. pc = -1.16 V) are product waves of B and A, respectively.
45. pa = -0.97 V) is a product of E. The two-electron nature of E was confirmed by bulk electrolysis studies. For example, bulk electrochemical reduction of 0.0228 g of 1 at an applied potential of -2.20 V using a platinum-basket electrode required 5.983 C (1.92 faraday/ equiv).
46. The electrolysis was conducted in acetonitrile solution using a platinum-basket working electrode.
47. The number of faradays per equivalent ranged from 2.12 to 2.66 when the applied potential was set in the range 0.44-0.69 V. Typically 21-25 mg of 1 was used in the bulk electrolysis experiments.
48. Isolation of the furan from electrolysis experiments was conducted as follows. After the acetonitrile solvent was removed, toluene was added to the residue and the resulting mixture was filtered, thereby separating most of the supporting electrolyte from the product. Chromatography of the toluene solution was conducted under a nitrogen atmosphere on a silica gel column using 5% ethyl acetate-95% benzene (v/v) as the eluting solution.
49. pc = -2.66 V on a glassy-carbon working electrode. This wave is not shown in the potential window of Figure 1.
50. CV scans of the butenolide 2 under the same experimental conditions show a chemically irreversible reduction wave at -1.96 V. This wave is not present in CV scans obtained after oxidation of 1.
51. All chemical oxidations were conducted under a nitrogen atmosphere.