Mechanistic studies of Si-CN and C-NC bond activation of silylnitriles and alkyl isonitriles by rhodium porphyrin radical: Novel cyanide transfer

Organometallics

Volumn 25, Issue 22, 2006, Pages 5381-5389

  Zhang, Lirong ^a   Fung, Chun Wah ^a   Chan, Kin Shing ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; CHEMICAL BONDS; CONCENTRATION (PROCESS); CYANIDES; PORPHYRINS; RATE CONSTANTS; SILICON;

ISONITRILES; PYRIDINES; REACTANTS; SILYLNITRILES;

ORGANOMETALLICS;

EID: 33751439214     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0605276     Document Type: Article

References (53)

1. Sherry, A. E.; Wayland, B. B. J. Am. Chem. Soc. 1990, 112, 1259-1261.
2. (a) Wayland, B. B.; Ba, S.; Sherry, A. E. J. Am. Chem. Soc. 1991, 113, 5305-5311.
3. (b) Del Rossi, K. J.; Zhang, X. X.; Wayland, B. B. J. Organomet. Chem. 1995, 504, 47-56.
4. (c) Del, Rossi, K. J.; Wayland, B. B. J. Chem. Soc., Chem. Commun. 1986, 1653-1655.
5. Wayland, B. B.; Poszmik, G.; Fryd, M. Organometallics 1992, 11, 3534-3542.
6. Anderson, J. E.; Yao, C.-L.; Kadish, K. M. Inorg. Chem. 1986, 25, 718-719.
7. Poszmik, G.; Carroll, P. J.; Wayland, B. B. Organometallics 1993, 12, 3410-3417.
8. (a) Farnos, M. D.; Woods, B. A.; Wayland, B. B. J. Am. Chem. Soc. 1986, 108, 3659-3663.
9. (b) Wayland, B. B.; Van Voorhees, S. L.; Wilker, C. Inorg. Chem. 1986, 25, 4039-4024.
10. (c) Van Voorhees, S. L.; Wayland, B. B. Organometallics 1985, 4, 1887-1888.
11. Farnos, M. D.; Woods, B. A.; Wayland, B. B. J. Am. Chem. Soc. 1986, 108, 3659-3663.
12. (a) Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 2, 91-100.
13. (b) Selmeczy, A. D.; Jones, W. D.; Osman, R.; Perutz, R. N. Organometallics 1995, 14, 5677-5685.
14. Wayland, B. B.; Sherry, A. E. Bunn, A. G. J. Am. Chem. Soc. 1993, 115, 7675-7684.
15. Collman, J. P.; Boulvtov, R. J. Am. Chem. Soc. 2000, 122, 11812-11821.
16. Ni, Y.; Fitzgerald, J. P.; Carroll, P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029-2035.
17. Wayland, B. B.; Balkus, K. J., Jr.; Farnos, M. D. Organometallics 1989, 8, 950-955.
18. Tse, M. K.; Chan, K. S. Dalton 2001, 510-511.
19. Mak, K. W.; Yeung, S. K.; Chan, K. S. Organometallics 2002, 21, 2362-2364.
20. Sakkai, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373-2381.
21. (a) Churchill, D.; Shin, J. H.; Hascall, T.; Hahn, J. M.; Bridgewater, B. M.; Parkin, G. Organometallics 1999, 18, 2403-2406.
22. (b) Taw, F. L.; White, P. S.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2002, 124, 4192-4193.
23. (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4660-4668.
24. (b) Huang, D.; Heyn, R. H.; Bollinger, J. C.; Caulton, K. G. Organometallics 1997, 16, 292-293.
25. Chan, K. S.; Zhang, L.; Fung, C. W. Organometallics 2004, 23, 6097-6098.
26. Zanchini, C. Chem. Phys. 2000, 254, 187-202.
27. Corey. J. Y. In The Chemistry of Organic Silicon Compounds Part 1; Patai, S., Rappoport, Z., Ed.; John Wiley & Sons Ltd.: New York, 1989; pp 5-6.
28. Tables of Interatomic Distances and Configuration in Molecules and Ions; The Chemical Society: London, 1958.
29. Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
30. Tse, A. K.-S.; Wu, B.-M.; Mak, T. C. W.; Chan, K. S. J. Organomet. Chem. 1998, 568, 257-261.
31. Halpern, J. Acc. Chem. Res. 1970, 3, 386-392.
32. (a) Collman, J. P.; Boulatov, R. J. Am. Chem. Soc. 2000, 122, 11812-11821.
33. (b) Marzilli, L. G.; Marzilli, P. A.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 5752-5753.
34. Mak, K. W.; Chan, K. S. J. Am. Chem. Soc. 1998, 120, 9686-9687.
35. (a) Pestovsky, O.; Bakac, A. Inorg. Chem. 2002, 41, 3975-3982.
36. (b) Acharyya, R.; Dutta, S.; Basuli, F.; Peng, S.-M.; Lee, G.-H.; Falvello, L. R.; Bhattacharya, S. Inorg. Chem. 2006, 45, 1252-1259.
37. (c) Osakada, K.; Koizumi, T.-a.; Yamamoto, T. Bull. Chem. Soc. Jpn. 1997, 70, 189-195.
38. (d) Wang, Z.-Q.; Turner, M. L.; Taylor, B. F.; Maitlis, P. M. Polyhedron 1995, 14, 2767-2769.
39. Bither, T. A.; Knoth, W. H.; Lindsey, R. V., Jr.; Sharkey, W. H. J. Am. Chem. Soc. 1958, 80, 4150-4153.
40. Rüchardt, C.; Meier, M.; Haaf, K.; Pakusch, J.; Wolber E. K. A.; Müller, B. Angew. Chem. 1991, 30, 893-1050.
41. Seyferth, D.; Kahlen, N. J. Am. Chem. Soc. 1960, 82, 1080-1082.
42. Hertler, W. R.; Dixon, D. A.; Matthews, E. W.; Davidson, F.; Kitson, F. G. J. Am. Chem. Soc. 1987, 109, 6532-6533.
43. Schneider, P. W.; Phelan, P. F.; Halpern, J. J. Am. Chem. Soc. 1969, 91, 77-81.
44. Castro, C. E.; Kray, W. C., Jr. J. Am. Chem. Soc. 1963, 85, 2768-2773.
45. Halpern, J.; Maher, J. P. J. Am. Chem. Soc. 1965, 87, 5361-5366.
46. Halpern, J.; Phelan, P. F. J. Am. Chem. Soc. 1972, 94, 1881-1886.
47. (a) Anderson, J. E.; Yao, C.; Kadish, K. M. J. Am. Chem. Soc. 1987. 109, 1106-1111.
48. (b) Giese, B.; Hartung, J.; Kesselheim, C.; Lindner, H. J.; Svoboda, I. Chem. Ber. 1993, 126, 1193-1200.
49. Wayland, B. B.; Sherry, A. E.; Poszmik, G.; Bunn, A. G. J. Am. Chem. Soc. 1992, 114, 1673-1681.
50. Paonessa, R. S.; Thomas, N. C.; Halpern, J. J. Am. Chem. Soc. 1985, 107, 4333-4335.
51. Huheey, J. E. Inorganic Chemistry, 2nd ed.; Harper & Row: New York, 1978; p 460.
52. Perkampus H. H. UV-Vis Spectroscopy and Its Applications; Springer-Verlag: Berlin, 1992.
53. Atkins. P. Physical Chemistry, 6th ed.; Oxford, 1998.