Synthesis, spectroscopy, and structure of àfamily of iridabenzenes generated by the reaction of Vaska-type complexes with a nucleophilic 3-vinyl-1-cyclopropene

Organometallics

Volumn 22, Issue 16, 2003, Pages 3279-3289

  Gilbertson, Robert D ^a   Lau, Thomas L S ^a   Lanza, Seren ^a   Wu, He Ping ^a   Weakley, Timothy J R ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

BENZENE; HEATING; ISOMERIZATION; MOLECULAR STRUCTURE; SOLUTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ORGANOMETALLICS;

EID: 0043076432     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030394d     Document Type: Article

References (74)

1. (a) Garratt, P. J. Aromaticity; Wiley: New York, 1986.
2. (b) Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity; Wiley: New York, 1994.
3. (c) Aromaticity. Chem. Rev. 2001, 101(5).
4. (a) Thorn, D. L.; Hoffmann, R. Nouv. J. Chim. 1979, 3, 39-45.
5. See also: (b) Iron, M. A.; Martin, J. M. L.; van der Boom, M. E. Chem. Commun. 2003, 132-133.
6. (c) Effertz, U.; Englert, U.; Podewils, F.; Salzer, A.; Wagner, T.; Kaupp, M. Organometallics 2003, 22, 264-274.
7. Bleeke, J. R. Chem. Rev. 2001, 101, 1205-1227.
8. Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606-623.
9. (a) Elliot, G. P.; Roper, W. R.; Waters, J. M. J. Chem. Soc., Chem. Commun. 1982, 811-813.
10. (b) Elliot, G. P.; Mcauley, N. M.; Roper, W. R. Inorg. Synth. 1989, 26, 184-189.
11. (c) Rickard, C. E. F.; Roper, W. R.; Woodgate, S. D.; Wright, L. J. Angew. Chem., Int. Ed. 2000, 39, 750-752.
12. Inter alia: (a) Lin, W.; Wilson, S. R.; Girolami, G. S. Organometallics 1997, 16, 2356-2361.
13. (b) Hein, J.; Jeffery, J. C.; Sherwood, P.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1987, 2211-2218.
14. (c) Kralik, M. S.; Rheingold, A. L.; Ernst, R. D. Organometallics 1987, 6, 2612-2614.
15. (d) Bertling, U.; Englert, U.; Salzer, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1003-1004.
16. (e) Englert, U.; Podewils, F.; Schiffers, I.; Salzer, A. Angew. Chem., Int. Ed. 1998, 37, 2134-2136.
17. Inter alia: (a) Chen, J.; Daniels, L. M.; Angelici, R. J. J. Am. Chem. Soc. 1990, 112, 199-204.
18. (b) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1993, 115, 2731-2742.
19. (c) Weller, K. J.; Filippov, I.; Briggs, P. M.; Wigley, D. E. Organometallics 1998, 17, 322-329.
20. (d) Bleeke, J. R.; Blanchard, J. M. B.; Donnay, E. Organometallics 2001, 20, 324-336.
21. (e) Bleeke, J. R.; Hinkle, P. V. Organometallics 2001, 20, 1939-1951.
22. Examples of transient metallabenzenes, inter alia: (a) Chin, R. M.; Jones, W. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 357-358.
23. (b) Yang, J.; Jones, W. M.; Dixon, J. K.; Allison, N. T. J. Am. Chem. Soc. 1996, 117, 9776-9777.
24. Bleeke, J. R. Acc. Chem. Res. 1991, 24, 271-277.
25. Gilbertson, R. D.; Weakley, T. J. R.; Haley, M. M. J. Am. Chem. Soc. 1909, 121, 2597-2598.
26. Gilbertson, R. D.; Weakley, T. J. R.; Haley, M. M. Chem. Eur. J. 2000, 6, 437-441.
27. See also: (a) Wu, H.-P.; Lanza, S.; Weakley, T. J. R.; Haley, M. M. Organometallics 2002, 21, 2824-2826.
28. (b) Jacob, V.; Weakley, T. J. R.; Haley, M. M. Angew. Chem., Int. Ed. 2002, 41, 3470-3473.
29. (c) Wu, H.-P.; Weakley, T. J. R.; Haley, M. M. Organometallics 2002, 21, 4320-4322.
30. (d) Jacob, V.; Weakley, T. J. R.; Haley, M. M. Organometallics 2002, 21, 5394-5400.
31. (a) Baird, M. S. Chem. Rev. 2003, 103, 1271-1294.
32. (b) Methods of Organic Chemistry (Houben-Weyl); de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 1996; Vol. E17d.
33. (c) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Happoport, Z., Ed.; Wiley: New York, 1987; pp 1223-1339.
34. (a) Goldschmidt, Z. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, pp 495-695.
35. (b) Binger, P.; Büch, H. M. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer-Verlag: Berlin, 1987; Vol. 135, pp 77-151.
36. (a) Binger, P.; Muller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610-611.
37. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974-3975.
38. (c) Gagne, M. R.; Grubbs, R. H.; Feldman, J.; Ziller, J. W. Organometallics 1992, 11, 3933-3935.
39. (d) Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1998, 115, 8130-8145.
40. (e) Flatt, B. T.; Grubbs, R. H.; Blanski, R. L.; Calabrese, J. C.; Feldman, J. Organometallics 1994, 13, 2728-2732.
41. (f) Li, R. T.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 10032-10040.
42. (a) Hermond, R. C.; Hughes, R. P.; Robinson, D. J.; Rheingold, A. L. Organometallics 1988, 7, 2239-2241.
43. (b) Hughes, R. P.; King, M. E.; Robinson, D. J.; Spotts, J. M. J. Am. Chem. Soc. 1989, 111, 8919-8920.
44. (c) Binger, P.; Muller, P.; Hermann, A. T.; Phillips, P.; Gabor, B.; Langhau, F. Chem. Ber. 1991, 124, 2165-2170.
45. (a) Hughes, R. P.; Trujillo, H. A.; Gauri, A. J. Organometallics 1995, 14, 4319-4324 and references therein.
46. (b) Donovan-Merkert, B. T.; Tjiong, H. I.; Rhinehart, L. M.; Russell, R. A.; Malik, J. Organometallics 1997, 16, 819-821.
47. (a) Haley, M. M.; Biggs, B.; Looney, W. A.; Gilbertson, R. D. Tetrahedron Lett. 1995, 36, 3457-3460.
48. (b) Gilbertson, R. D.; Haley, M. M.; Weakley, T. J. R.; Weiss, H.-C.; Boese, R. Organometallics 1998, 17, 3105-3107.
49. (c) Gilbertson, R. D.; Weakley, T. J. R.; Haley, M. M. J. Org. Chem. 2000, 65, 1422-1430.
50. (d) Gilbertson, R. D.; Wu, H.-P.; Gorman-Lewis, D.; Weakley, T. J. R.; Weiss, H.-C.; Boese, R.; Haley, M. M. Submitted for publication.
51. (e) Gilbertson, R. D.; Bercot, E. A.; Sohill, B.; Haley, M. M. Unpublished results.
52. Hughes, R. P.; Robinson, D. J. Organometallics 1989, 8, 1015-1019.
53. (a) Smithers, R. H. J. Org. Chem. 1978, 43, 2833-2838.
54. (b) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021-4024.
55. (a) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173-2174.
56. (b) Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261-5262.
57. Burk, M. J.; Crabtree, R. H. Inorg. Chem. 1986, 25, 931-932.
58. Schwartz, J.; Hart, D. W.; McGiffert, B. J. Am. Chem. Soc. 1974, 96, 5613-5614.
59. In our earlier reports we used EtOH to quench the reaction. This was subsequently shown to affect the ratio of 13 to 14 initially produced.
60. 2-π complex versus metallacyclopropane), see ref 11.
61. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
62. (a) Housecroft, C. E.; Sharpe, A. G. Inorganic Chemistry, Prentice Hall: London, 2001.
63. (b) Spessard, G. O.; Miessler, G. L. Organometallic Chemistry; Prentice Hall: London, 1997.
64. (c) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
65. Boese, R. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: London, 1992; Vol. 2, pp 191-254.
66. Bleeke, J. R.; Xie, Y.-P.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703-4704.
67. Gilbertson, E. D. Ph.D. Thesis, University of Oregon, 1999.
68. (a) Wiedemann, R.; Steinert, P.; Schäfer, M.; Werner, H. J. Am. Chem. Soc. 1993, 115, 9864-9865.
69. (b) Wiedemann, R.; Wolf, J.; Werner, H. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1244-1246.
70. (c) Wiedemann, R.; Wolf, J.; Werner, H. J. Chem. Ber. 1986, 129, 29-31.
71. (d) Werner, H.; Wiedemann, R.; Stainert, P.; Wolf, J. Chem. Eur. J. 1997, 3, 127-137.
72. Christi, M. Angew. Chem., Int. Ed. Engl. 1981, 20, 529-546 and references therein.
73. 31P NMR data all support such a structure. We are currently attempting to obtain an X-ray crystal structure: Wu, H.-P.; Haley, M. M. Unpublished results.
74. Williams, R. V.; Braden, D. A.; Haley, M. M. Unpublished results.