New forms of coordinated carbon: Wirelike cumulenic C3 and C5 sp carbon chains that span two different transition metals and mediate charge transfer

Journal of the American Chemical Society

Volumn 120, Issue 43, 1998, Pages 11071-11081

  Bartik, Tamás ^a   Weng, Weiqing ^a   Ramsden, James A ^a   Szafert, Slawomir ^a   Falloon, Stephen B ^a   Arif, Atta M ^a   Gladysz, J A ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; MANGANESE DERIVATIVE; RHENIUM COMPLEX;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTALLOGRAPHY; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SPECTROSCOPY; SURFACE CHARGE; SYNTHESIS;

EID: 0032483699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981927q     Document Type: Article

References (98)

1. General reviews or accounts: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (d) Bruce, M. I. Coord. Chem. Rev. 1997, 166, 91. (e) Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
2. General reviews or accounts: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (d) Bruce, M. I. Coord. Chem. Rev. 1997, 166, 91. (e) Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
3. General reviews or accounts: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (d) Bruce, M. I. Coord. Chem. Rev. 1997, 166, 91. (e) Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
4. General reviews or accounts: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (d) Bruce, M. I. Coord. Chem. Rev. 1997, 166, 91. (e) Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
5. General reviews or accounts: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969. (d) Bruce, M. I. Coord. Chem. Rev. 1997, 166, 91. (e) Balch, A. L.; Olmstead, M. M. Chem. Rev. 1998, 98, 2123.
6. 1 complexes of the type I: (a) Goedken, V. L.; Deakin, M. R.; Bottomly, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Latesky, S. L.; Selegue, J. P. J. Am. Chem. Soc. 1987, 109, 4731. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 318. (d) Etienne, M.; White, P. S.; Templeton. J. L. J. Am. Chem. Soc. 1991, 113, 2324. (e) Miller, R. L.; Wolczanski, P. T.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10422.
7. 1 complexes of the type I: (a) Goedken, V. L.; Deakin, M. R.; Bottomly, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Latesky, S. L.; Selegue, J. P. J. Am. Chem. Soc. 1987, 109, 4731. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 318. (d) Etienne, M.; White, P. S.; Templeton. J. L. J. Am. Chem. Soc. 1991, 113, 2324. (e) Miller, R. L.; Wolczanski, P. T.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10422.
8. 1 complexes of the type I: (a) Goedken, V. L.; Deakin, M. R.; Bottomly, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Latesky, S. L.; Selegue, J. P. J. Am. Chem. Soc. 1987, 109, 4731. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 318. (d) Etienne, M.; White, P. S.; Templeton. J. L. J. Am. Chem. Soc. 1991, 113, 2324. (e) Miller, R. L.; Wolczanski, P. T.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10422.
9. 1 complexes of the type I: (a) Goedken, V. L.; Deakin, M. R.; Bottomly, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Latesky, S. L.; Selegue, J. P. J. Am. Chem. Soc. 1987, 109, 4731. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 318. (d) Etienne, M.; White, P. S.; Templeton. J. L. J. Am. Chem. Soc. 1991, 113, 2324. (e) Miller, R. L.; Wolczanski, P. T.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10422.
10. 1 complexes of the type I: (a) Goedken, V. L.; Deakin, M. R.; Bottomly, L. A. J. Chem. Soc., Chem. Commun. 1982, 607. (b) Latesky, S. L.; Selegue, J. P. J. Am. Chem. Soc. 1987, 109, 4731. (c) Beck, W.; Knauer, W.; Robl, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 318. (d) Etienne, M.; White, P. S.; Templeton. J. L. J. Am. Chem. Soc. 1991, 113, 2324. (e) Miller, R. L.; Wolczanski, P. T.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10422.
11. 2 complexes: Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1995, 68, 420.
12. Preliminary communications of this work: (a) Weng, W.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 3824.
13. (b) Weng, W.; Bartik, T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2199.
14. 3 complexes of the type I: Woodworth, B. E.; Templeton, J. L. J. Am. Chem. Soc. 1996, 118, 7418.
15. 4 complexes of the type I reported through 1996 are cited in refs 6a,b; refs 6c-e describe more recent reports: (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775. (b) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (c) Woodworth, B. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1997, 119, 828. (d) Gil-Rubio, J.; Laubender, M.; Werner, H. Organometallics 1998, 17, 1202 (e) Guillemot, M.; Toupet, L.; Lapinte, C. Organometallics 1998, 17, 1928.
16. 4 complexes of the type I reported through 1996 are cited in refs 6a,b; refs 6c-e describe more recent reports: (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775. (b) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (c) Woodworth, B. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1997, 119, 828. (d) Gil-Rubio, J.; Laubender, M.; Werner, H. Organometallics 1998, 17, 1202 (e) Guillemot, M.; Toupet, L.; Lapinte, C. Organometallics 1998, 17, 1928.
17. 4 complexes of the type I reported through 1996 are cited in refs 6a,b; refs 6c-e describe more recent reports: (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775. (b) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (c) Woodworth, B. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1997, 119, 828. (d) Gil-Rubio, J.; Laubender, M.; Werner, H. Organometallics 1998, 17, 1202 (e) Guillemot, M.; Toupet, L.; Lapinte, C. Organometallics 1998, 17, 1928.
18. 4 complexes of the type I reported through 1996 are cited in refs 6a,b; refs 6c-e describe more recent reports: (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775. (b) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (c) Woodworth, B. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1997, 119, 828. (d) Gil-Rubio, J.; Laubender, M.; Werner, H. Organometallics 1998, 17, 1202 (e) Guillemot, M.; Toupet, L.; Lapinte, C. Organometallics 1998, 17, 1928.
19. 4 complexes of the type I reported through 1996 are cited in refs 6a,b; refs 6c-e describe more recent reports: (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775. (b) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (c) Woodworth, B. E.; White, P. S.; Templeton, J. L. J. Am. Chem. Soc. 1997, 119, 828. (d) Gil-Rubio, J.; Laubender, M.; Werner, H. Organometallics 1998, 17, 1202 (e) Guillemot, M.; Toupet, L.; Lapinte, C. Organometallics 1998, 17, 1928.
20. 2O complexes of the type I: (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477. (c) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (d) Bruce, M. I.; Ke, Mingzhc; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (e) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882.
21. 2O complexes of the type I: (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477. (c) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (d) Bruce, M. I.; Ke, Mingzhc; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (e) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882.
22. 2O complexes of the type I: (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477. (c) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (d) Bruce, M. I.; Ke, Mingzhc; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (e) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882.
23. 2O complexes of the type I: (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477. (c) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (d) Bruce, M. I.; Ke, Mingzhc; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (e) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882.
24. 2O complexes of the type I: (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655. (b) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477. (c) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414. (d) Bruce, M. I.; Ke, Mingzhc; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (e) Akita, M.; Chung, M.-C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882.
25. 3 ligands: (a) Morton, M. S.; Selegue, J. P. J. Am. Chem. Soc. 1995, 117, 7005. (b) Falloon, S. B.; Weng, W.; Arif, A. M.; Gladysz, J. A. Organometallics 1997, 16, 2008. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033.
26. 3 ligands: (a) Morton, M. S.; Selegue, J. P. J. Am. Chem. Soc. 1995, 117, 7005. (b) Falloon, S. B.; Weng, W.; Arif, A. M.; Gladysz, J. A. Organometallics 1997, 16, 2008. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033.
27. 3 ligands: (a) Morton, M. S.; Selegue, J. P. J. Am. Chem. Soc. 1995, 117, 7005. (b) Falloon, S. B.; Weng, W.; Arif, A. M.; Gladysz, J. A. Organometallics 1997, 16, 2008. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033.
28. Astruc, D. Electron Transfer and Radical Processes in Transition Metal Chemistry; VCH: New York, 1995; Part I.
29. See the following 1996-7 articles, and reviews cited therein: (a) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311. (b) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406. (c) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497. (d) Tamm, M.; Grzegorzewski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (e) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
30. See the following 1996-7 articles, and reviews cited therein: (a) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311. (b) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406. (c) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497. (d) Tamm, M.; Grzegorzewski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (e) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
31. See the following 1996-7 articles, and reviews cited therein: (a) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311. (b) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406. (c) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497. (d) Tamm, M.; Grzegorzewski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (e) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
32. See the following 1996-7 articles, and reviews cited therein: (a) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311. (b) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406. (c) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497. (d) Tamm, M.; Grzegorzewski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (e) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
33. See the following 1996-7 articles, and reviews cited therein: (a) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311. (b) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406. (c) LeCours, S. M.; Guan, H.-W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497. (d) Tamm, M.; Grzegorzewski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (e) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
34. Ward, M. D. Chem. Ind. 1997, 640 and refs 1 and 2 therein.
35. (b) Harriman, A.; Ziessel, R. J. Chem. Soc., Chem. Commun. 1996, 1707.
36. (c) Andres, R. P.; Bielefeld, J. D.; Henderson, J. I.; Janes, D. B.; Kolagunta, V. R.; Kubiak, C. P., Mahoney, W. J.; Osifchin, R. G. Science 1996, 273, 1690.
37. (d) Astruc, D. Acc. Chem. Res. 1997, 30, 383.
38. Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163.
39. Fischer, H. In Carbyne Complexes; Fischer, H., Hofmann, P., Kreibl, F. R., Schrock, R. R., Schubert, U., Weiss, K., Eds.; VCH: New York, 1988; Chapter 1.
40. 5 complexes have recently been investigated: (a) Hartbaum, C.; Roth, G.; Fischer, H. Chem. Ber./Recl. 1997, 130, 479. (b) Hartbaum, C.; Fischer, H. Chem. Ber./Recl. 1997, 130, 1063.
41. 5 complexes have recently been investigated: (a) Hartbaum, C.; Roth, G.; Fischer, H. Chem. Ber./Recl. 1997, 130, 479. (b) Hartbaum, C.; Fischer, H. Chem. Ber./Recl. 1997, 130, 1063.
42. Ramsden, J. A.; Weng, W.; Gladysz, J. A. Organometallics 1992, 11, 3635.
43. Reimer, K. J.; Shaver, A. J. Organomet. Chem. 1975, 93, 243.
44. Welch, S. A.; Heeg, M. J.; Winter, C. H. Organometallics 1994, 13, 1865.
45. 2, see: Fischer, E. O.; Chen, J.; Scherzer, K. J. Organomet. Chem. 1983, 253, 231 and references therein.
46. 2, see: Fischer, E. O.; Chen, J.; Scherzer, K. J. Organomet. Chem. 1983, 253, 231 and references therein.
47. 2, see: Fischer, E. O.; Chen, J.; Scherzer, K. J. Organomet. Chem. 1983, 253, 231 and references therein.
48. Weng, W.; Bartik, T.; Johnson, M. T.; Arif, A. M.; Gladysz, J. A. Organometallics 1995, 14, 889.
49. (a) Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865. Solvent dependence data are given in footnote 40 of ref 6a.
50. (b) Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096.
51. (a) McDermott, G. A.; Dorries, A. M.; Mayr, A. Organometallics 1987, 6, 925.
52. (b) Hart, I. J.; Hill, A. F.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1989, 2261.
53. 8b The ReC, ReC≡C, and ReC≡CC bond lengths are very close to those of 3 (1.983(7), 1.238(9), and 1.364(10) Å).
54. (a) Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79.
55. (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; pp 21-22.
56. This represents the average for 32 such complexes (R, R′ restricted to carbon substituents) in the January 1997 Cambridge Crystallographic Data Base (range 2.275(8)-2.10(2) Å).
57. (a) Casey, C. P.; Polichnowski, S. W.; Tuinstra, H. E.; Albin, L. D.; Calabrese, J. C. Inorg. Chem. 1978, 17, 3045.
58. (b) Darensbourg, D. J.; Bauch, C. G.; Rheingold, A. L. Inorg. Chem. 1987, 26, 977.
59. 5]-(48.2 Hz; Darensbourg, D. J.; Grötsch, G. J. Am. Chem. Soc. 1985, 107, 7473).
60. 5]-(48.2 Hz; Darensbourg, D. J.; Grötsch, G. J. Am. Chem. Soc. 1985, 107, 7473).
61. (a) Handwerker, B. M.; Garrett, K. E.; Nagle, K. L.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 1562.
62. (b) Terry, M. R.; Mercando, L. A.; Kelley, C.; Geoffroy, G. L.; Nombel, P.; Lugan, N.; Mathieu, R.; Ostrander, R. L.; Owens-Waltermire, B. E.; Rheingold, A. L. Organometallics 1994, 13, 843.
63. (a) Berke, H. Chem. Ber. 1980, 113, 1370.
64. (b) Kolobava, N. E.; Ivanov, L. L.; Zhvanko, O. S. Izu. Akad. Nauk SSSR, Ser. Khim. 1980, 478, 2646.
65. (a) Fischer, E. O.; Meineke, E. W.; Kreissl, F. R. Chem. Ber. 1977, 110, 1140.
66. (b) Fischer, E. O.; Postonov, V. N.; Kreissl, F. R. J. Organomet. Chem. 1982, 231, C73.
67. Berke, H.; Huttner, G.; Seyerl, J. v. Z. Naturforsch., B: Anorg. Chem., Org. Chem., 1981, 36, 1277.
68. Berke, H.; Huttner, G.; Seyerl, J. v. J. Organomet. Chem 1981, 218, 193.
69. Kolobova, N. E.; Ivanov, L. L.; Zhvanko, O. S.; Khitrova, O. M.; Batsanov, A. S.; Struchkov, Yu. T. J. Organomet. Chem. 1984, 262, 39.
70. 4: (a) Petz, W.; Weller, F. Z. Naturforsch. 1996, 51b, 1598.
71. (b) Berke, H.; Grössmann, U.; Huttner, L.; Zsolnai, L. Chem. Ber. 1984, 117, 3432.
72. Anderson, S.; Hill, A. F. Organometallics 1995, 14, 1562.
73. Eastmond, R.; Johnson, T. R.; Walton, D. R. M. J. Organomet. Chem. 1973, 50, 87.
74. (a) Gamasa, M. P.; Gimeno, J.; Godefroy, I.; Lastra, E.; Martin-Vaca, B. M.; Garcia-Granda, S.; Gutierrez-Rodriguez, A. J. Chem. Soc., Dalton Trans. 1995, 1901.
75. (b) Kawata, Y.; Sato, M. Organometallics 1997, 16, 1093.
76. (c) Dahlenburg, L.; Weiss, A.; Bock, M.; Zahl, A. J. Organomet. Chem. 1997, 541, 465.
77. Xia, H. P.; Wu, W. F.; Ng, W. S.; Williams, I. D.; Jia, G. Organometallics 1997, 16, 2940.
78. (a) Bublitz, G. U.; Ortiz, R.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 3365 and references therein.
79. (b) Tolbert, L. M.; Zhao, X. J. Am. Chem. Soc. 1997, 119, 3253.
80. Graham, E. M.; Miskowski, V. M.; Perry, J. W.; Coulter, D. R.; Stiegman, A. E.; Schaefer, W. P.; March, R. E. J. Am. Chem. Soc. 1989, 111, 8771.
81. Wright, R. E.; Vogler, A. J. Organomet. Chem. 1978, 160, 197.
82. Wootton, J. L.; Zink, J. I. J. Am. Chem. Soc. 1997, 119, 1895 and references therein.
83. (a) Bruneau, C.; Dixneuf, P. H. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.-in-Chief; Roberts, S. M., Volume Ed; Pergamon: New York, 1995; Chapter 1.20 and reviews cited therein,
84. (b) Bildstein, B.; Schweiger, M.; Kopacka, H.; Ongania, K.-H.; Wurst, K. Organometallics 1998, 17, 2414.
85. (a) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129.
86. (b) Le Narvor, N.; Lapinte, C. C. R. Acad. Sci. Paris, Ser. IIc, in press.
87. (a) Touchard, D.; Maquette, P.; Daridor, A.; Toupet, L.; Dixneuf, P. H. J. Am. Chem. Soc. 1994, 116, 11157.
88. (b) Kovacik, I.; Laubender, M.; Werner, H. Organometallics 1997, 16, 5607 and references therein.
89. (c) Roth, G.; Fischer, H. Organometallics 1996, 15, 1139.
90. Szafert, S.; Haquette, P. Unpublished data, University of Utah.
91. Roth, G.; Fischer, H. Organometallics 1996, 15, 5766.
92. Peters, T.; Bohling, J.; Martin-Alvarez, J. M. Unpublished data, University of Utah.
93. -1).
94. Positive FAB, mlz for most intense peak of isotope envelope; relative intensities are for the specified mass range.
95. 13C signals are not observed.
96. 2): 224.0/ 224.7 (s, CO), 103.5/103.7 (s, CCl), 81.7/82.4, 80.6/81.3 (2 s, CH).
97. Frenz, B. A. The Enraf-Nonius CAD 4 SDP - A Real-time System for Concurrent X-ray Data Collection and Crystal Structure Determination. In Computing and Crystallography; Schenk, H., Olthof-Hazelkamp, R., van Konigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978; pp 64-71.
98. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974; Vol. IV, pp 72-98, 149-150, Tables 2.2B and 2.3.1.