Direct synthesis of an iridabenzene from a nucleophilic 3-vinyl-1- cyclopropene [1]

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2597-2598

  Gilbertson, Robert D ^a   Weakley, Timothy J R ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ORGANOMETALLIC COMPOUND;

CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033599512     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984420o     Document Type: Letter

References (26)

1. (a) Goldschmidt, Z. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1995; Vol. 2, pp 495-695.
2. (b) Binger, P.; Büch, H. M. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer-Verlag: Berlin, 1987; Vol. 135, pp 77-151.
3. For a comprehensive review of cyclopropenes, see: (a) Methods of Organic Chemistry (Houben-Weyl), de Meijere, A., Ed.; Thieme: Stuttgart, 1996; Vol. E17d.
4. (b) Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley; New York, 1987; pp 1223-1339.
5. (a) Binger, P.; Muller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610-611.
6. (b) Nguyen, S. T.; Johnson, L. K., Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974-3975.
7. (c) Gagne, M. R.; Grubbs, R. H.; Feldman, J.; Ziller, J. W. Organometallics 1992, 11, 3933-3935.
8. (d) Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130-8145.
9. (e) Flatt, B. T., Grubbs, R. H.; Blanski, R. L.; Calabrese, J. C.; Feldman, J. Organometallics 1994, 13, 2728-2732.
10. (f) Li, R. T.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 10032-10040.
11. (a) Hermond, R. C.; Hughes, R. P.; Robinson, D. J.; Rheingold, A. L. Organometallics 1988, 7, 2239-2241.
12. (b) Hughes, R. P.; King, M. E.; Robinson, D. J.; Spotts, J. M. J. Am. Chem. Soc. 1989, 111, 8919-8920.
13. (c) Binger, P.; Muller, P.; Hermann, A. T.; Phillips, P.; Gabor, B.; Langhau, F. Chem. Ber. 1991, 124, 2165-2170.
14. Hughes, R. P.; Trujillo, H. A.; Gauri, A. J. Organometallics 1995, 14, 4319-4324 and references therein.
15. Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606-623 and references therein.
16. Thorn, D. L.; Hoffmann, R. Nouv. J. Chim. 1979, 3, 39-45.
17. 2; C, 67.41; H, 4.50. Found: C. 66.89; H. 4.43.
18. Hughes, R. P.; Robinson, D. J. Organometallics 1989, 8, 1015-1019.
19. (a) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173-2174.
20. (b) Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261-5262.
21. Cycloaddition reactions involving iridabenzene 4 are described in ref 6.
22. Schwartz, J.; Hart, D. W.; McGiffert, B. J. Am. Chem. Soc. 1974, 96, 5613-5614.
23. For a discussion concerning the interconversion of metallacyclobutenes and vinylcarbene complexes see: Doxsee, K. M.; Juliette, J. J. J.; Mouser, J. K. M.; Zientara, K. Organometallics 1993, 12, 4742-4744.
24. 2-cyclopropenes to metal carbenes has been observed. See ref 3d and: Fischer, H.; Hofmann, J.; Mauz, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 998-999.
25. 2-cyclopropene complexes to metallacyclobulenes has been observed. See ref 4c.
26. 2Ir(CO)Cl does not coordinate with 2 in benzene at ambient temperature.