Ring-methyl activation in pentamethylcyclopentadienyl complexes. 5. Syntheses and structures of tetramethylfulvene complexes of ruthenium(II)

Organometallics

Volumn 15, Issue 1, 1996, Pages 98-104

  Fan, Li ^a   Wei, Chunghong ^a   Aigbirhio, Franklin I ^a   Turner, Michael L ^a   Gusev, Oleg V ^a,b   Morozova, Larissa N ^a,b   Knowles, Daniel R T ^a   Maitlis, Peter M ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002282919     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950462z     Document Type: Article

References (46)

1. Part 4: Fan, L.; Turner, M. L.; Adams, H.; Bailey, N. A.; Maitlis, P. M. Organometallics 1995, 14, 676.
2. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
3. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
4. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
5. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
6. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
7. Miguel-Garcia, J. A.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1990, 1472. Gusev, O. V.; Rubezhov, A. Z.; Miguel-Garcia, J. A.; Maitlis, P. M. Mendeleev Commun. 1991, 21. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Organomet. Chem. 1991, 413, 427. Miguel-Garcia, J. A.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1992, 131. See also for H/D exchange: Kang, J. W.; Maitlis, P. M. J. Organomet. Chem. 1971, 30, 127. Hirai, K.; Nutton, A.; Maitlis, P. M. J. Mol. Catal. 1981,10, 203.
8. Hamon, J.-R.; Astruc, D. Organometallics 1988, 7, 1036. Astruc, D.; Roman, E.; Hamon, J.-R.; Batail, P. J. Am. Chem. Soc. 1979, 101, 2240. Astruc, D.; Hamon, J.-R.; Roman, E.; Michaud, P. J. Am. Chem. Soc. 1981, 103, 7502. Astruc, D. Acc. Chem. Res. 1991, 24, 36.
9. Hamon, J.-R.; Astruc, D. Organometallics 1988, 7, 1036. Astruc, D.; Roman, E.; Hamon, J.-R.; Batail, P. J. Am. Chem. Soc. 1979, 101, 2240. Astruc, D.; Hamon, J.-R.; Roman, E.; Michaud, P. J. Am. Chem. Soc. 1981, 103, 7502. Astruc, D. Acc. Chem. Res. 1991, 24, 36.
10. Hamon, J.-R.; Astruc, D. Organometallics 1988, 7, 1036. Astruc, D.; Roman, E.; Hamon, J.-R.; Batail, P. J. Am. Chem. Soc. 1979, 101, 2240. Astruc, D.; Hamon, J.-R.; Roman, E.; Michaud, P. J. Am. Chem. Soc. 1981, 103, 7502. Astruc, D. Acc. Chem. Res. 1991, 24, 36.
11. Hamon, J.-R.; Astruc, D. Organometallics 1988, 7, 1036. Astruc, D.; Roman, E.; Hamon, J.-R.; Batail, P. J. Am. Chem. Soc. 1979, 101, 2240. Astruc, D.; Hamon, J.-R.; Roman, E.; Michaud, P. J. Am. Chem. Soc. 1981, 103, 7502. Astruc, D. Acc. Chem. Res. 1991, 24, 36.
12. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
13. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
14. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
15. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
16. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
17. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
18. Werner, H.; Crisp, G. T.; Jolly, P. W.; Kraus, H.-J.; Krueger, C. Organometallics 1983, 2, 1370. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1985, 107, 7758. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818. Glueck, D. S.; Bergman, R. G. Organometallics 1990, 9, 2862. Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3246. Luinstra, G. A.; Teuben, J. H. J. Am. Chem. Soc. 1992, 114, 3361. Horton, A. D. Organometallics 1992, 11, 3271.
19. Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232. McDade, C.; Brock, C. P.; Bercaw, J. E. Organometallics 1982, 1, 1629.
20. Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232. McDade, C.; Brock, C. P.; Bercaw, J. E. Organometallics 1982, 1, 1629.
21. Fan, L.; Turner, M. L.; Hursthouse, M. B.; Malik, K. M. A.; Gusev, O. V.; Maitlis, P. M. J. Am. Chem. Soc. 1994, 116, 385. Full details of the crystal structure determination of 3a are given in the Supporting Information to that paper or may be obtained from the Cambridge Crystallographic Data Centre.
22. Wei, C.; Aigbirhio, F.; Adams, H.; Bailey, N. A.; Hempstead, P. D.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1991, 883.
23. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274. Oshima, N.; Suzuki, H.; Mor-Oka, Y. Chem. Lett. 1984, 1161. Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267. Koelle, U.; Kossakowski, J.; Klaff, N.; Wesemann, L.; Englert, U.; Herberich, G. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 690.
24. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274. Oshima, N.; Suzuki, H.; Mor-Oka, Y. Chem. Lett. 1984, 1161. Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267. Koelle, U.; Kossakowski, J.; Klaff, N.; Wesemann, L.; Englert, U.; Herberich, G. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 690.
25. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274. Oshima, N.; Suzuki, H.; Mor-Oka, Y. Chem. Lett. 1984, 1161. Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267. Koelle, U.; Kossakowski, J.; Klaff, N.; Wesemann, L.; Englert, U.; Herberich, G. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 690.
26. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274. Oshima, N.; Suzuki, H.; Mor-Oka, Y. Chem. Lett. 1984, 1161. Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267. Koelle, U.; Kossakowski, J.; Klaff, N.; Wesemann, L.; Englert, U.; Herberich, G. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 690.
27. Rao, K. M.; Day, C. L.; Jacobson, R. A.; Angelici, R. J. Organometallics 1992, 11, 2303.
28. Geary, W. G. Coord. Chem. Rew. 1971, 7, 81.
29. Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232.
30. Yanovsky, A. I.; Struchkov, Y. T.; Kreindlin, A. Z.; Rybinskaya, M. I. J. Organomet. Chem. 1989, 369, 125. Kreindlin, A. Z.; Petrovskii, P. V.; Rybinskaya, M. I.; Yanovsky, A. I.; Struchkov, Y. T. J. Organomet. Chem. 1987, 319, 229.
31. Yanovsky, A. I.; Struchkov, Y. T.; Kreindlin, A. Z.; Rybinskaya, M. I. J. Organomet. Chem. 1989, 369, 125. Kreindlin, A. Z.; Petrovskii, P. V.; Rybinskaya, M. I.; Yanovsky, A. I.; Struchkov, Y. T. J. Organomet. Chem. 1987, 319, 229.
32. Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267.
33. Klahn, A. H.; Moore, M. H.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1992, 1699.
34. 15 The major isomer is that found in the X-ray structure determination, and the authors suggest that the minor isomer forms from this on dissolution. No interconversion between the two on the NMR time scale was noted.
35. Wang, M. H.; Englert, U.; Koelle, U. J. Organomet. Chem. 1993, 453, 127.
36. 9 however the bond lengths and angles are sufficiently different to make it clear that the two are not identical and, therefore, that 3a is not a contaminant of 1a.
37. Maitlis, P. M. Chem. Soc. Rev. 1981, 10, 1.
38. See, for example: Cloke, F. G. N.; Day, J. P.; Green, J. C.; Morley, C. P.; Swain, A. C. J. Chem. Soc., Dalton Trans. 1991, 789.
39. Ittel, S. D.; Ibers, J. A. Adv. Organomet. Chem. 1976, 14, 33.
40. Consiglio, G.; Morandini, F.; Ciani, G.; Sironi, A. Angew. Chem., Int. Ed. Engl. 1983, 22, 333. Lindsay, C.; Cesarotti, E.; Adams, H.; Bailey, N. A.; White, C. Organometallics 1990, 9, 2594.
41. Consiglio, G.; Morandini, F.; Ciani, G.; Sironi, A. Angew. Chem., Int. Ed. Engl. 1983, 22, 333. Lindsay, C.; Cesarotti, E.; Adams, H.; Bailey, N. A.; White, C. Organometallics 1990, 9, 2594.
42. Simandi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
43. For example, see references cited by: Astruc, D. Chem. Rev. 1988, 88, 1189. Hoard, D. W.; Sharp, P. R. Inorg. Chem. 1993, 32, 612.
44. For example, see references cited by: Astruc, D. Chem. Rev. 1988, 88, 1189. Hoard, D. W.; Sharp, P. R. Inorg. Chem. 1993, 32, 612.
45. 2 which initiates in step (8) is recovered in step (11), the cycle only requires a trace of oxygen.
46. These are assigned to the symmetrical isomer, e.g., (Figure 5).