Synthesis of 2,2',3,3'-tetramethyl- and 2,2',3,3'-tetra-tert- butylfulvalene: Attractive platforms for dinuclear transition metal fragments, as exemplified by (η5:η5-2,2',3,3'-t-BU 4C10H4)M2(CO)n (M = Fe, Ru, Os, Mo) and first x-ray crystal structures of fulvalene diiron and diosmium complexes

Synthesis

Volumn , Issue 19, 2005, Pages 3373-3379

  Zhu, Bolin ^a,b   Miljanić, Ognjen Š ^a,b   Vollhardt, K Peter C ^a,b   West, Michael J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

Fulvalene complexes; Isomerizations; Pentafulvalene; Photochemistry; Transition metals

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; IRRADIATION; ISOMERIZATION; MOLECULAR STRUCTURE; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

FULVALENE COMPLEXES; LIGANDS; PENTAFULVALENE;

TRANSITION METALS;

2,2',3,3' TETRA TERT BUTYLFULVALENE; 2,2',3,3' TETRAMETHYLFULVALENE; ALKENE DERIVATIVE; CHEMICAL COMPOUND; CYCLOPENTADIENE DERIVATIVE; IRON; IRON DERIVATIVE; LIGAND; METAL DERIVATIVE; OSMIUM; OSMIUM DERIVATIVE; RUTHENIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; IRRADIATION; ISOMER; ISOMERIZATION; PHOTOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 29144437180     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918438     Document Type: Article

References (68)

1. See, inter alia: (a) Toyota, A.; Koseki, S. J. Phys. Chem. A 1998, 102, 6668.
2. (b) Scott, A. P.; Agranat, I.; Biedermann, P. U.; Riggs, N. V.; Radom, L. J. Org. Chem. 1997, 62, 2026.
3. (c) Aihara, J. J. Chem. Soc., Perkin Trans. 2 1996, 2185.
4. For a review, see: (a) Heck, J.; Dabek, S.; Meyer-Friedrichsen, T.; Wong, H. Coord. Chem. Rev. 1999, 790-792, 1217. For recent work, see, among others:
5. (b) Hong, S. Y.; Kim, S. C. Bull. Korean Chem. Soc. 2003, 24, 1649.
6. (c) Benassi, R.; Taddei, F. J. Mol. Struct. (Theochem) 2001, 572, 169.
7. (d) Hinchliffe, A.; Soscún Machado, H. J. Int. J. Mol. Sci. 2000, 1, 39.
8. (e) Hinchliffe, A.; Perez, J. J.; Soscún Machado, H. J. Elec. J. Theor. Chem. 1997, 2, 325.
9. For recent reviews, see: (a) Ceccon, A.; Santi, S.; Orian, L.; Bisello, A. Coord. Chem. Rev. 2004, 248, 683.
10. (b) De Azevedo, C. G.; Vollhardt, K. P. C. Synlett 2002, 1019.
11. (a) Doering, W. v. E. In Theoretical Organic Chemistry: The Kekulé Symposium; Butterworths: London, 1959, 35.
12. (b) DeMore, W. B.; Pritchard, H. O.; Davidson, N. J. Am. Chem. Soc. 1959, 81, 5874.
13. (c) Scherer, K. V. Jr. J. Am. Chem. Soc. 1963, 85, 1550.
14. (d) Bitman, G. L.; Aristova, V. G.; Popkov, K. K.; Skorokhodov, I.I. Zh. Org. Khim. 1967, 3, 495.
15. (e) Escher, A.; Rutsch, W.; Neuenschwander, M. Helv. Chim. Acta. 1986, 69, 1644.
16. For an early review, see: Bergmann, E. D. Chem. Rev. 1968, 68, 41.
17. (a) Mark, V. Tetrahedron. Lett. 1961, 333.
18. (b) West, R.; Kwitowski, P. T. J. Am. Chem. Soc. 1968, 90, 4697.
19. (c) Banks, R. E.; Bridge, M.; Haszeldine, R. N.; Roberts, D. W.; Tucker, N. I. J. Chem. Soc. C 1970, 2531.
20. (d) Abel, E. W.; Pring, G. M. Inorg. Chim. Acta 1980, 44, L161.
21. (a) Pauson, P. L.; Williams, B. J. J. Chem. Soc. 1961, 4153.
22. (b) Prinzbach, H.; Sauter, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 133.
23. (c) Prinzbach, H.; Sauter, H.; Hörster, H.-G.; Limbach, H.-H.; Knothe, L. Liebigs Ann. Chem. 1977, 869.
24. (a) Brand, R.; Krimmer, H.-P.; Lindner, H.-J.; Sturm, V.; Hafner, K. Tetrahedron Lett. 1982, 23, 5131.
25. (b) Sitzmann, H.; Bollmann, C.; Dehmlow, E. V. Tetrahedron Lett. 1994, 35, 5619.
26. Davies, A. G.; Lusztyk, E.; Lusztyk, J. J. Chem. Soc., Perkin Trans. 2 1982, 729.
27. (a) Tilset, M.; Vollhardt, K. P. C.; Boese, R. Organometallics 1994, 13, 3146.
28. (b) Hirao, T.; Kurashina, M.; Aramaki, K.; Nishihara, H. J. Chem. Soc., Dalton Trans. 1996, 2929.
29. (c) Delgado, S.; Macazaga, M. J.; Medina, R. M.; Moreno, C.; González-Velasco, J.; Marcos, M. L.; Farrar, D. H.; Ramachandran, R. Organometallics 1996, 15, 5416.
30. (d) Marcos, M. L.; Moreno, C.; Medina, R. M.; Macazaga, M.-J.; Delgado, S.; González-Velasco, J. J. Organomet. Chem. 1998, 568, 185.
31. (e) Bauer, A.; Hilbig, H.; Hiller, W.; Hinterschwepfinger, E.; Köhler, F. H.; Neumayer, M. Synthesis 2001, 778.
32. Conia, J. M.; Leriverend, M. L. Bull. Soc. Chim. Fr. 1970, 2981.
33. For a review, see: Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2442.
34. (a) Doering, W. v. E.; Beasley, G. H. Tetrahedron 1973, 29, 2231.
35. (b) Metzner, P.; Vialle, J. Bull. Soc. Chim. Fr. 1973, 1703.
36. (a) Hughes, R. P.; Kowalski, A. S.; Lomprey, J. R.; Neithamer, D. R. J. Org. Chem. 1996, 61, 401.
37. (b) Hughes, R. P.; Lomprey, J. R. Inorg. Chim. Acta 1995, 240, 653.
38. (c) Hughes, R. P.; Kowalski, A. S.; Lomprey, J. R.; Rheingold, A. L. Organometallics 1994, 13, 2691.
39. Hedaya, E.; McNeil, D. W.; Schissel, P.; McAdoo, D. J. J. Am. Chem. Soc. 1968, 90, 5284.
40. (a) Hilbig, H.; Köhler, F. H. Z. Naturforsch., B 2000, 55, 1099.
41. (b) Moberg, C. Acta Chem. Scand., Ser B 1978, 32, 149.
42. Zhu, B.; Miljanić, O. Š.; Vollhardt, K. P. C.; West, M. J., to be published.
43. See, among others: (a) Boese, R.; Cammack, J. K.; Matzger, A. J.; Pflug, K.; Tolman, W. B.; Vollhardt, K. P. C.; Weidman, T. W. J. Am. Chem. Soc. 1997, 119, 6757.
44. (b) Jutzi, P.; Schnittger, J.; Dahlhaus, J.; Gestmann, D.; Leue, H.-C. J. Organomet. Chem. 1991, 415, 117.
45. (c) Jutzi, P.; Schnittger, J.; Wieland, W.; Neumann, B.; Stammler, H.-G. J. Organomet. Chem. 1991, 415, 425.
46. (d) Jutzi, P.; Schnittger, J.; Neumann, B.; Stammler, H.-G. J. Organomet. Chem. 1991, 410, C13.
47. (e) Jutzi, P.; Schnittger, J.; Hursthouse, M. B. Chem. Ber. 1991, 124, 1693.
48. (f) Jutzi, P.; Schnittger, J. Chem. Ber. 1989, 122, 629.
49. 6, see: (a) Vollhardt, K. P. C.; Weidman, T. W. Organometallics 1984, 3, 82.
50. 4, see:
51. Bister, H.-J.; Butenschön, H. Synlett 1992, 22.
52. 2, M = Fe, Ru, Os, see: (a) Bitterwolf, T. E. Coord. Chem. Rev. 2000, 206-207, 419.
53. (b) Bitterwolf, T. E.; Linehan, J. C.; Shade, J. E. Organometallics 2001, 20, 775.
54. For a single osmocene moiety in a termetallocene chain, see: Jaitner, P.; Schottenberger, H.; Gamper, S.; Obendorf, D. J. Organomet. Chem. 1994, 475, 113.
55. Wang, B.; Zhu, B.; Zhang, J.; Xu, S.; Zhou, X.; Weng, L. Organometallics 2003, 22, 5543; and references therein.
56. Bryan, R. F.; Greene, P. T.; Newlands, M. J.; Field, D. S. J. Chem. Soc. A 1970, 3068; and references therein.
57. Cited as unpublished in: Albers, M. O.; Robinson, D. J.; Singleton, E. Coord. Chem. Rev. 1987, 79, 1.
58. Brumaghim, J. L.; Priepot, J. G.; Girolami, G. S. Organometallics 1999, 18, 2139.
59. Gross, C. L.; Wilson, S. R.; Girolami, G. S. J. Am. Chem. Soc. 1994, 116, 10294.
60. Hoyano, J. K.; Graham, W. A. G. J. Am. Chem. Soc. 1982, 104, 3722.
61. Droege, M. W.; Harman, W. D.; Taube, H. Inorg. Chem. 1987, 26, 1309.
62. (a) Howell, J. A.; Rowan, A. J. J. Chem. Soc., Dalton Trans. 1980, 503.
63. (b) Fischer, R. D.; Vogler, A.; Noack, K. J. Organomet. Chem. 1967, 7, 135.
64. This paper cites a crystal structure determination by O. S. Mills in progress.
65. For a review, see: Esteruelas, M. A.; Lopez, A. M. Organometallics 2005, 24, 3584.
66. CCDC-278400 and CCDC-278401 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk).
67. SIR97: Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115.
68. DIRDIF94: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-94 Program System, Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands, 1994.