Synthesis, characterization, and isomerization of an iridabenzvalene

Chemistry - A European Journal

Volumn 6, Issue 3, 2000, Pages 437-441

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

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Aromaticity; Iridium; Metallacycles; Strained molecules; Valence isomerization

Indexed keywords

BENZENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; HALOGEN; IRIDIUM COMPLEX; METAL; SILVER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034603152     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000204)6:3<437::AID-CHEM437>3.0.CO;2-M     Document Type: Article

References (45)

1. For complementary historical overviews of this area, see: a) I. Gutman, J. H. Potgieter, J. Chem. Educ. 1994, 71, 222-224;
2. b) J. H. Potgieter, J. Chem. Educ. 1991, 68, 280-281.
3. See, for example: a) P. J. Garratt, Aromaticity, Wiley, New York, 1986;
4. b) V. I. Minkin, M. N. Glukhovtsev, B. Y. Simkin, Aromaticity and Antiaromaticity, Wiley, New York, 1994;
5. c) Y. Kobayashi, I. Kumadaki, Top. Curr. Chem. 1984, 125, 103-150;
6. d) A. T. Balaban, Rev. Roum. Chim. 1966, 11, 1097-1116;
7. e) D. S. Warren, B. M. Gimarc, J. Am. Chem. Soc. 1992, 114, 5378-5385.
8. M. Regitz, H. Heydt, U. Bergsträsser in Advances in Strain in Organic Chemistry, Vol. 5 (Ed.: B. Halton), JAI Press, London, 1996, pp. 161-243, and references therein.
9. D. L. Thorn, R. Hoffmann, Nouv. J. Chim. 1979, 3, 39-45.
10. a) G. P. Elliott, W. R. Roper, J. M. Waters, J. Chem. Soc. Chem. Commun. 1982, 811-813;
11. b) G. P. Eiliott, N. M. McAuley, W. R. Roper, Inorg. Synth. 1989, 26, 184-189;
12. c) J. R. Bleeke, Y.-F. Xie, W.-J. Peng, M. Y. Chiang, J. Am. Chem. Soc. 1989, 111, 4118-4120;
13. d) J. R. Bleeke, Acc. Chem. Res. 1991, 24, 271-277;
14. e) J. R. Bleeke, R. Behm, Y-F. Xie, M. Y. Chiang, K. D. Robinson, A. M. Beatty, Organometallics 1997, 16, 606-623;
15. f) J. R. Bleeke, R. Behm, J. Am. Chem. Soc. 1997, 111, 8503-8511;
16. g) J. Yang, W. M. Jones, J. K. Dixon, N. T. Allison, J. Am. Chem. Soc. 1995, 117, 9776-9777.
17. a) M. S. Kralik, A. L. Rheingold, R. D. Ernst, Organometallics 1987, 6, 2612-2614;
18. b) H. W. Bosch, H.-U. Hund, D. Nieltlispach, A. Salzer, Organometallics 1992, 11, 2087-2098;
19. c) J. R. Bleeke, L. A. Bass, Y.-F. Xie, M. Y. Chiang, J. Am. Chem. Soc. 1992, 114, 4213-4219;
20. d) W. Lin, S. R. Wilson, G. S. Girolami, J. Chem. Soc. Chem. Commun. 1993, 284-285;
21. e) U. Bertling, U Englert, A. Salzer, Angew. Chem. 1994, 106, 1026-1028; Angew. Chem. Int. Ed. Engl. 1994, 33, 1003-1005;
22. e) U. Bertling, U Englert, A. Salzer, Angew. Chem. 1994, 106, 1026-1028; Angew. Chem. Int. Ed. Engl. 1994, 33, 1003-1005;
23. f) W. Lin, S. R. Wilson, G. S. Girolami, Organometallics 1997, 16, 2356-2361;
24. g) U. Englert, F. Podewils, I. Schiffers, A. Salzer, Angew. Chem. 1998, 110, 2196-2197; Angew. Chem. Int. Ed. 1998, 37, 2134-2136.
25. g) U. Englert, F. Podewils, I. Schiffers, A. Salzer, Angew. Chem. 1998, 110, 2196-2197; Angew. Chem. Int. Ed. 1998, 37, 2134-2136.
26. R. D. Gilbertson, T. J. R. Weakley, M. M. Haley, J. Am. Chem. Soc. 1999, 121, 2597-2598.
27. J. Schwartz, D. W. Hart, B. McGiffert, J. Am. Chem. Soc. 1974, 96, 5613-5614.
28. For a general review of cyclopropene transition metal complexes, see: Z. Goldschmidt in The Chemistry of the Cyclopropyl Group, Vol. 2, (Ed.: Z. Rappoport), Wiley, New York, 1995, pp. 495-695.
29. R. T. Li, S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1994, 116, 10032-10040.
30. R. P. Hughes, J. W. Reisch, A. L. Rheingold, Organometallics 1985, 4, 241-244.
31. J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987.
32. R. Boese in Advances in Strain in Organic Chemistry, Vol. 2 (Ed.: B. Halton), JAI Press, London, 1992, pp. 191-254.
33. a) L. K. Johnson, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1993, 115, 8130-8145;
34. b) D. L. Hughes, G. J. Leigh, C. N. McMahon, J. Chem. Soc. Dalton Trans. 1997, 1301-1307.
35. For a review of benzvalene chemistry, see: M. Christi, Angew. Chem. 1981, 93, 515-532; Angew. Chem. Int. Ed. Engl. 1981, 20, 529-546.
36. For a review of benzvalene chemistry, see: M. Christi, Angew. Chem. 1981, 93, 515-532; Angew. Chem. Int. Ed. Engl. 1981, 20, 529-546.
37. a) P. Binger, P. Muller, R. Benn, R. Mynott, Angew. Chem. 1989, 101, 647-648; Angew. Chem. Int. Ed. Engl. 1989, 28, 610-611;
38. a) P. Binger, P. Muller, R. Benn, R. Mynott, Angew. Chem. 1989, 101, 647-648; Angew. Chem. Int. Ed. Engl. 1989, 28, 610-611;
39. b) S. T. Nguyen, L. K. Johnson, R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 3974-3975;
40. c) M. R. Gagne, R. H. Grubbs, J. Feldman, J. W Ziller, Organometallics 1992, 11, 3933-3935;
41. d) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728-2732.
42. N. J. Turro, C. A. Renner, T. J. Katz, K. B. Wiberg, H. A. Connon, Tetrahedron Lett. 1976, 4133-4136.
43. 4 showed that complex 5 remained unchanged after several hours in acetonitrile.
44. A. Padwa, T. J. Blacklock, R. Loza, J. Org. Chem. 1982, 47, 3712-3721.
45. M. J. Burk, R. H. Crabtree, Inorg. Chem. 1986, 25, 931-932.