Carbonyl-substituted nickelocenes by the cross-metathesis route

Organometallics

Volumn 28, Issue 23, 2009, Pages 6838-6840

  Buchowicz, Włodzimierz ^a   Szmajda, Magdalena ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; CROSS METATHESIS; CYCLOPENTADIENYLS; HIGH YIELD; METHOXY; METHYL ACRYLATES; METHYL VINYL KETONES; MONOCLINIC CRYSTAL SYSTEMS; NICKELOCENE; SPACE GROUPS;

FLUORINE CONTAINING POLYMERS; KETONES;

SYNTHESIS (CHEMICAL);

EID: 71949119397     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9008444     Document Type: Article

References (42)

1. Fischer, E. O.; Jira, K. Z. Naturforsch. B. 1953, 8, 217.
2. Pasynkiewicz, S.; Pietrzykowski, A. Coord. Chem. Rev. 2002, 231, 199.
3. Jolly, P. W. In Comprehensive Organometallic Chemistry; Pergamon Press: Oxford, 1982; Vol. 6, Chapter 37.8.
4. 5Tl. See: Kläui, W.; Ramacher, L. Angew. Chem., Int. Ed. Engl. 1986, 25, 97.
5. For a synthesis of a cyclopentadienyl methyl ester see: Gendron, R. A. L.; Berg, D. J.; Barclay, T. Can. J. Chem. 2002, 80, 1285.
6. Hart, W. P.; Macomber, D.W.; Rausch, M. D. J. Am. Chem. Soc. 1980, 102, 1196.
7. Conway, G. B.; Rausch, M. D. Organometallics 1985, 4, 688.
8. Fischer, R. A.; Nlate, S.; Hoffmann, H.; Herdtweck, E.; Blümel, J. Organometallics 1996, 15, 5746.
9. (a) Bauer, E. B.; Gladysz, J. A. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol 2, pp 403-431, and references therein.
10. (b) Shima, T.; Hampel, F.; Gladysz, J. A. Angew. Chem., Int. Ed. 2004 ,43, 5537.
11. (c) Shima, T.; Bauer, E. B.; Hampel, F.; Gladysz, J. A. Dalton Trans. 2004, 1012.
12. (d) Dralle, K.; Jaffa, N. L.; le Roex, T.; Moss, J. R.; Travis, S.; Watermeyer, N. D.; Sivaramakrishna, A. Chem. Commun. 2005, 3865.
13. (e) Kuwabara, J.; Takeuchi, D.; Osakada, K. Organometallics 2005, 24, 2705.
14. (f) Chen, W.-Z.; Protasiewicz, J. D.; Davis, S. A.; Updegraff, J. B.; Ma, L.-Q.; Fanwick, P. E.; Ren, T. Inorg. Chem. 2007, 46, 3775.
15. (g) Hess, G. D.; Hampel, F.; Gladysz, J. A. Organometallics 2007, 26, 5129.
16. (h) Alhomaidan, O.; Bai, G.; Stephan, D. W. Organometallics 2008, 27, 6343.
17. (i) Skopek, K.; Gladysz, J. A. J. Organomet. Chem. 2008, 693, 857.
18. (a) Locke, A. J.; Jones, C.; Richards, C. J. J. Organomet. Chem. 2001, 637-639, 669.
19. (b) Ogasawara, M.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 9068.
20. (c) Ogasawara, M.; Nagano, T.; Hayashi, T. Organometallics 2003, 22, 1174.
21. (d) Ogasawara, M.; Watanabe, S.; Fan, L.; Nakajima, K.; Takahashi, T. Organometallics 2006, 25, 5201.
22. (e) Weychardt, H.; Plenio, H. Organometallics 2008, 27, 1479.
23. Buchowicz, W.; Jerzykiewicz, L. B.; Krasiñska, A.; Losi, S.; Pietrzykowski, A.; Zanello, P. Organometallics 2006, 25, 5076.
24. (a) Seshadri, H.; Lovely, C. J. Org. Lett. 2000, 2, 327.
25. (b) Yasuda, T.; Abe, J.; Iyoda, T.; Kawai, T. Chem. Lett. 2001, 812.
26. (c) Yasuda, T.; Abe, J.; Yoshida, H.; Iyoda, T.; Kawai, T. Adv. Synth. Catal. 2002, 344, 705.
27. (d) Suzaki, Y.; Osakada, K. Dalton Trans. 2007, 2376.
28. 2IMes)] is active for cross-metathesis of α,β-unsaturated carbonyl compounds with terminal olefins; therefore the second-generation catalyst was used in all experiments; see:
29. (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
30. (b) Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
31. 3) ppm.
32. SDBSWeb: http://riodb01.ibase.aist.go.jp/sdbs/(National Institute of Advanced Industrial Science and Technology, September 18, 2009).
33. (a) Köhler, F. H. J. Organomet. Chem. 1976, 110, 235.
34. (b) Scroggins, W. T.; Rettig, M. F.; Wing, R. M. Inorg. Chem. 1976, 15, 1381.
35. (c) Gattinger, I.; Herker, M. A.; Hiller, W.; Köhler, F. H. Inorg. Chem. 1999, 38, 2359.
36. (d) Herker, M.; Köhler, F. H.; Schwaiger, M.; Weber, B. J. Organomet. Chem. 2002, 658, 266.
37. Seiler, P.; Dunitz, J. D. Acta Crystallogr. 1980, B36, 2255.
38. Vos, D.; Salmon, A.; Stammler, H.-G.; Neumann, B.; Jutzi, P. Organometallics 2000, 19, 3874.
39. (a) Castellani, M. P.; Gelb, S. J.; Rheingold, A. I.; Trogier, W. C. Organometallics 1987, 6, 1703.
40. (b) Zanin, I. E.; Antipin, M. Yu. Kristallografiya 2001, 46, 1030.
41. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: New York, 1988.
42. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.