Syntheses of various (arylimido)vanadium(V)-dialkyl complexes containing aryloxo and alkoxo ligands, and ring-opening metathesis polymerization using a vanadium(V)-alkylidene complex

Organometallics

Volumn 27, Issue 15, 2008, Pages 3818-3824

  Nomura, Kotohiro ^a   Onishi, Yoshifumi ^a   Fujiki, Michiya ^a   Yamada, Junji ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COMPUTER NETWORKS; MONOMERS; POLYMERS; TRANSITION METALS; VANADIUM ALLOYS;

ALKYLIDENE; DIALKYL COMPLEXES; RING-OPENING METATHESIS POLYMERIZATION; VANADIUM;

VANADIUM COMPOUNDS;

EID: 50549095966     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800284d     Document Type: Article

References (65)

1. For example (general text of metal-alkyl chemistry): (a) The Organometallic Chemistry of the Transition Metals, 4th ed.; Crabtree, R. H., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2005; p 53.
2. (b) Synthesis of Organometallic Compounds: A Practical Guide; Komiya, S., Ed.; John Wiley & Sons Ltd.: West Sussex, England, 1997.
3. Related reviews for olefin polymerization catalysts (including vanadium complexes): (a) Gambarotta, S. Coord. Chem. Rev. 2003, 237, 229.
4. (b) Hagen, H.; Boersma, J.; van Koten, G. Chem. Soc. Rev. 2002, 31, 357.
5. (c) Bolton, P. D.; Mountford, P. Adv. Synth. Catal. 2005, 347, 355.
6. (d) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
7. (e) Nomura, K. In New Developments in Catalysis Research; BevyL. P., Ed.; Nova Science Publishers, Inc.: New York, 2005; p 199.
8. For examples, see:(a) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
9. (b) Grubbs, R. H., Ed. Handbook of Metathesis; Wiley-VCH: Weinheim, Germany, 2003; Vol. 13.
10. (c) Khosravi, E., Szymanska-Buzar, T., Eds. Ring-Opening Metathesis Polymerisation and Related Chemistry; Kluwer: Dordrecht, The Netherlands, 2002.
11. (d) Imamoglu, Y., Dragutan, V., Eds. Metathesis Chemistry; Springer: Dordrecht, The Netherlands, 2007.
12. For examples, see:(a) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158.
13. (b) Schrock, R. R. In Alkene Metathesis in Organic Synthesis; FürstnerA., Ed.;Springer: Berlin, Germany, 1998; p 1.
14. (c) SchrockR. R. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 1, p 8.
15. For examples, see:(a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
16. (b) Nguyen, S. T.; Trnka, T. M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 3, pp 61-85.
17. Pioneering examples:(a) Carrick, W. L. J. Am. Chem. Soc. 1958, 80, 6455.
18. (b) Carrick, W. L.; Kluiber, R. W.; Bonner, E. F.; Wartman, L. H.; Rugg, F. M.; Smith, J. J. J. Am. Chem. Soc. 1960, 82, 3883.
19. (c) Junghanns, V. E.; Gumboldt, A.; Bier, G. Makromol. Chem. 1962, 58, 18.
20. (d) Carrick, W. L.; Reichle, W. T.; Pennella, F.; Smith., J. J. J. Am. Chem. Soc. 1960, 82, 3887.
21. (e) Natta, G.; Mazzanti, G.; Valvassori, A.; Sartori, G.; Fiumani, D. J. Polym. Sci. 1961, 51, 411.
22. (f) Gumboldt, V. A.; Helberg, J.; Schleitzer, G. Makromol. Chem. 1967, 101, 229.
23. (g) Lehr, M. H. Macromolecules 1968, 1, 178.
24. (h) Christman, D. L.; Keim, G. I. Macromolecules 1968, 1, 358.
25. (i) Christman, D. L. J. Polym. Sci., Polym. Chem. Ed. 1972, 10, 471.
26. Pioneering examples for synthesis of block copolymers by living polymerization using vanadium catalysts:(a) Doi, Y.; Ueki, S.; Soga, K. Macromolecules 1979, 12, 814.
27. (b) Doi, Y.; Hizal, G.; Soga, K. Makromol. Chem. 1987, 188, 1273.
28. Some structural characterizations, reaction chemistry of V(III),(IV) methyl complex:(a) Hessen, B.; Teuben, J. H.; Lemmen, T. H.; Huffman, J. C.; Caulton, K. G. Organometallics 1985, 4, 946.
29. (b) Hessen, B.; Lemmen, T. H.; Luttikhedde, H. J. G.; Teuben, J. H.; Petersen, J. L.; Jagner, S.; Huffman, J. C.; Caulton, K. G. Organometallics 1987, 6, 2354.
30. (c) Hessen, B.; Meetama, A.; Teuben, J. H. J. Am. Chem. Soc. 1989, 111, 5977.
31. (d) Gerlach, C. P.; Arnold, J. Organometallics 1996, 15, 5260.
32. (e) Aharonian, G.; Feghali, K.; Gambarotta, S.; Yap, G. P. A. Organometallics 2001, 20, 2616.
33. (f) Feghali, K.; Harding, D. J.; Reardon, D.; Gambarotta, S.; Yap, G.; Wang, Q. Organometallics 2002, 21, 968.
34. (g) Choukroun, R.; Lorber, C.; Donnadieu, B. Organometallics 2002, 21, 1124.
35. (h) Liu, G.; Beetstra, D. J.; Meetsma, A.; Hessen, B. Organometallics 2004, 23, 3914.
36. Examples for structurally characterized V(V) alkyls:(a) de With, J.; Horton, A. D.; Orpen, A. G. Organometallics 1990, 9, 2207.
37. (b) Murphy, V. J.; Turner, H. Organometallics 1997, 16, 2495.
38. Examples:(a) Preuss, F.; Ogger, L. Z. Naturforsch. 1982, 37B, 957.
39. (b) Devore, D. D.; Lichtenhan, J. D.; Takusagawa, F.; Maatta, E. J. Am. Chem. Soc. 1987, 109, 7408.
40. (c) Preuss, F.; Becker, H.; Kraub, J.; Sheldrick, W. J. Z. Naturforsch. 1988, 43B, 1195.
41. (d) Preuss, F.; Becker, H.; Wieland, T. Z. Naturforsch. 1990, 45B, 191.
42. (e) Preuss, F.; Overhoff, G.; Becker, H.; Häusler, H. J.; Frank, W.; Reiss, G. Z. Anorg. Allg. Chem. 1993, 619, 1827.
43. (f) Solan, G. A.; Cozzi, P. G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1994, 13, 2572.
44. (g) Chan, M. C. W.; Cole, J. M.; Gibson, V. C.; Howard, J. A. K. Chem. Commun. 1997, 2345.
45. Our previous examples:(a) Yamada, J.; Nomura, K. Organometallics 2005, 24, 3621.
46. (b) Yamada, J.; Fujiki, M.; Nomura, K. Organometallics 2007, 26, 2579.
47. nBuLi as the catalyst, a ring-opened polymer was obtained.
48. Polymerization of cyclopentene:(a) Natta, G.; Dall'Asta, G.; Mazzanti, G. Angew. Chem. 1965, 76, 765.
49. (b) Natta, G.; Scaglione, P. Rubber Chem. Technol. 1969, 42, 1235. However, the resultant polymers were mixtures of polymers prepared by olefin metathesis and coordination insertion pathways.
50. Yamada, J.; Fujiki, M.; Nomura, K. Organometallics 2005, 24, 2248. References concerning the other vanadium-aklylidenes were also cited therein.
51. 10e were known as examples.
52. Some of these results were presented at the XVIIth International Symposium on Olefin Metathesis (ISOMXVII), July 2007, Pasadena, CA.
53. 3SH are shown in the Supporting Information.
54. Nomura, K.; Sagara, A.; Imanishi, Y. Macromolecules 2002, 35, 1583.
55. 13)N(H)Me did not take place.
56. Nomura, K.; Atsumi, T.; Fujiki, M.; Yamada, J. J. Mol. Catal. A 2007, 275, 1.
57. 3 under these conditions.
58. Review article for synthesis of early transition metal-alkylidenes: (a) Schrock, R. R. Chem. Rev. 2002, 102, 145.
59. (b) Mindiola, D. Acc. Chem. Res. 2006, 39, 813.
60. (c) Mindiola, D.; Bailey, B.; Basuli, F. Eur. J. Inorg. Chem. 2006, 16, 3135.
61. (a) Wang, W.; Yamada, J.; Fujiki, M.; Nomura, K. Catal. Commun. 2003, 4, 159.
62. (b) Wang, W.; Nomura, K. Macromolecules 2005, 38, 5905.
63. 3 (at 25°C) are shown in the Supporting Information.
64. 6 are shown in the Supporting Information.
65. Buijink, J.-K. F.; Teubin, J. H.; Kooijman, H.; Spek, A. L. Organometallics 1994, 13, 2922.