Formation of coordinated C-nitroso compounds by reaction of K[IrCl 5NO] with alkenes

Organometallics

Volumn 25, Issue 16, 2006, Pages 3799-3801

  Escola, Natalia ^a   Llebaría, Analuz ^a   Leitus, Gregory ^b   Doctorovich, Fabio ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; CRYSTAL STRUCTURE; OLEFINS; X RAY DIFFRACTION;

C-NITROSOCHLOROALKANES; CYCLOOCTENE; ELECTROPHILIC; NOCL;

POTASSIUM COMPOUNDS;

EID: 33746896160     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060141v     Document Type: Article

References (51)

1. (a) Filehne, W. Arch. Exptl. Pathol. Pharmakol. 1878, 9, 329-379.
2. (b) Loeb, R. F.; Bock, A. V.; Fitz, R. Am. J. Med. Sci. 1921, 161, 539-546.
3. (a) Schenkman, J. B.; Wilson, B. J.; Cinti, D. L. Biochem. Pharmacol. 1972, 21, 2373-2383.
4. (b) Franklin, M. R. Mol. Pharmacol. 1974, 10, 975-985.
5. (c) Mansuy, D.; Beaune, P.; Cresteil, T.; Bacot, C.; Chottard, J.-C.; Gans, P. Eur. J. Biochem. 1978, 86, 573-579.
6. (d) Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Chem. Rev. 2002, 102, 1019-1065.
7. Gowenlock, B. G.; Richter-Addo, G. B. Chem. Rev. 2004, 104, 3315-3340.
8. (a) Kraemer, G.; Spilker, A. Ber. Bunsen-Ges. Phys. Chem. 1896, 29, 552.
9. (b) Wilder, P., Jr.; Culberson, C. F.; Youngblood, G. T. J. Am. Chem. Soc. 1959, 81, 655-658.
10. Youngblood, G. T.; Trivette, C. D., Jr.; Wilder, P., Jr. J. Org. Chem. 1958, 23, 684-686.
11. (a) Miller, J. B. J. Org. Chem. 1961, 26, 4905-4907.
12. (b) Meinwald, J.; Meïnwald, Y. C.; Baker, T. N., III. J. Am. Chem. Soc. 1963, 85, 2513-2514.
13. (a) Swinehart, J. H.; Schmidt, W. G. Inorg. Chem. 1967, 6(2), 232-237.
14. (b) Wolfe, S. K.; Swinehart, J. H. Inorg. Chem. 1968, 7(9), 1855-1859.
15. (c) Butler, A. R.; Glidewell, C.; Chaipanieh, V.; McGinnis, J. J. Chem. Soc., Perkin Trans. 2 1986, 7-9.
16. (d) Butler, A. R.; Glidewell, C. Chem. Soc. Rev. 1987, 16, 361-380 and references therein.
17. Bottomley, P.; White, P. S.; Mukaida, M.; Shimura, K.; Kakihana, H. J. Chem. Soc., Dalton Trans. 1988, 2965-2969.
18. (a) Bowden, W. L.; Little, W. F.; Meyer, T. J. Salmon, D. J. Am. Chem. Soc. 1975, 97, 6897-6898.
19. (b) Bowden, W. L.; Little, W. F.; Meyer, T. J. J. Am. Chem. Soc. 1974, 96, 5605-5606.
20. (c) Bowden, W. L.; Little, W. F.; Meyer, T. J. J. Am. Chem. Soc. 1976, 98, 444-448.
21. Clamp, S.; Connelly, N. G.; Howard, J. A. K.; Manners, I.; Payne, J. D.; Geiger, W. E. J. Chem. Soc., Dalton Trans. 1984, 1659-1665.
22. (a) Brunner, H. J. Organomet. Chem. 1968, 12, 517-522.
23. (b) Brunner, H.; Loskot, S. Angew. Chem., Int. Ed. Engl. 1971, 10, 515-516.
24. (c) Brunner, H.; Loskot, S. J. Organomet. Chem. 1973, 61, 401-414.
25. (d) Becker, P. N.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 2985-2995.
26. (e) Becker, P. N.; Bergman, R. G. Organometallics 1983, 2(7), 787-796.
27. (a) Pilato, R. S.; McGettigan, C.; Geoffroy, G. L.; Rheingold, A. L.; Geib, S. J. Organometallics 1990, 9, 312-317.
28. (b) Mansuy, D.; Battioni, P.; Chottard, J.-C.; Riche, C.; Chiaroni, A. J. Am. Chem. Soc. 1983, 105, 455-463.
29. (c) Weiner, W. P.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 3922-3929.
30. (d) Weiner, W. P.; White, M. A.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3612-3614.
31. (e) Chang, J.; Seidler, M. D.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 3258-3271.
32. (f) Mansuy, D.; Dreme, M.; Chottard, J. C Guilhem, J. J. Organomet. Chem. 1978, 161, 207-220.
33. (g) Mansuy, D.; Dreme, M.; Chottard, J.-C.; Girault, J.-P.; Guilhem, J. J. Am. Chem. Soc. 1980, 102, 844-845.
34. (h) Sohl, C. D.; Lee, J.; Alguindigue, S. S.; Khan, M. A.; Richter-Addo, G. B. J. Inorg. Biochem. 2004, 98, 1238-1246.
35. -1.
36. 1/2 = -0.33 V vs ferrocene in butyronitrile: Sieger, M.; Sarkar, B.; Zališ, S.; Fiedler, J.; Escola, N.; Doctorovich, F.; Olabe, J.; Kaim, W. Dalton Trans. 2004, 1797-1800.
37. 4Cl present as an impurity).
38. w = 0.0356 (observed data with I > 2σ(I)).
39. Enemark, J. H.; Feltham, R. D. Coord. Chem. Rev. 1974, 13, 339-406.
40. Youngblood, G. T.; Trivette, C. D., Jr.; Wilder, P., Jr. J. Org. Chem. 1958, 23(5), 684-686.
41. Miller, J. B. J. Org. Chem. 1961, 26(12), 4905-4907.
42. Perissinotti, L. L.; Estrin, D. A.; Leitus, G.; Doctorovich, F. J. Am. Chem. Soc. 2006, 128, 2512-2513.
43. Doctorovich, F.; Di Salvo, F.; Escola, N.; Trápani, C.; Shimon, L. Organometallics, 2005, 24, 4707-4709.
44. Frisch, M. J.; et al. Gaussian 98, Rev. A7; Gaussian, Inc., Pittsburgh, PA, 1998. See the Supporting Information for the remaining 56 authors.
45. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
46. Lee, C.; Yang, W.; Parr, R., Phys. Rev. 1988, B37, 785-789.
47. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560-571.
48. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
49. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
50. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
51. The unreactive alkenes (and one alkyne) are as follows: fumaric acid, trans-cinnamic acid, citraconic acid, 2,3-dimethylmaleic anhydride, 2,4-hexadienoic acid, cis-2-pentenenitrile, 2-butinoic acid, and tetracyano- ethylene.