Tautomerization of methyldiazene to formaldehyde-hydrazone in ruthenium and osmium complexes

Inorganic Chemistry

Volumn 44, Issue 24, 2005, Pages 8947-8954

  Albertin, Gabriele ^a   Antoniutti, Stefano ^a   Bacchi, Alessia ^b   De Marchi, Fabiola ^a   Pelizzi, Giancarlo ^b  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28944444197     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic050817z     Document Type: Article

References (67)

1. (a) Sutton, D. Chem. Rev. 1993, 93, 995-1022.
2. (b) Kisch, H.; Holzmeier, P. Adv. Organomet. Chem. 1992, 34, 67-109.
3. (c) Zollinger, H., Ed. Diazo Chemistry II; VCH: Weinheim, Germany, 1995.
4. For some papers on coordinate diazene, see: (a) Sellmann, D.; Brandi, A.; Endell, R. Angew. Chem., Int. Ed. Engl. 1973, 12, 1019.
5. (b) Albertin, G.; Antoniutti, S.; Pelizzi, G.; Vitali, F.; Bordignon, E. J. Am. Chem. Soc. 1986, 108, 6627-6634.
6. (c) Smith, M. R., III; Hillhouse, G. L. J. Am. Chem. Soc. 1988, 110, 4066-4068.
7. (d) Sellmann, D.; Soglowek, W.; Knoch, F.; Moll, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1271-1272.
8. (e) Collmann, J. P.; Hutchinson, J. E.; Lopez, M. A.; Guilard, R.; Reed, R. A. J Am. Chem. Soc. 1991, 113, 2794-2796.
9. (f) Sellmann, D.; Käppler, J.; Moll, M.; Knoch, F. Inorg. Chem. 1993, 32, 960-964.
10. (g) Smith, M. R., III; Cheng, T.-Y.; Hillhouse, G. L. J. Am. Chem. Soc. 1993, 115, 8638-8642.
11. (h) Cheng, T.-Y.; Ponce, A.; Rheingold, A. L.; Hillhouse, G. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 657-659.
12. (i) Cheng, T.-Y.; Peters, J. C.; Hillhouse, G. L. J. Am. Chem. Soc. 1994, 116, 204-207.
13. (j) Albertin, G.; Antoniutti, S.; Bacchi, A.; Bordignon, E.; Busatto, F.; Pelizzi, G. Inorg. Chem. 1997, 36, 1296-1305.
14. (k) Sellmann, D.; Engl, K.; Heinemann, F. W.; Sieler, J. Eur. J. Inorg. Chem. 2000, 1079-1089.
15. (a) MacKay, B. A.; Fryzuk, M. D. Chem. Rev. 2004, 104, 385-401.
16. (b) Fryzuk, M. D.; Johnson, S. A. Coord. Chem. Rev. 2000, 200-202, 379-409.
17. (c) Hidai, M.; Mizobe, Y. Chem. Rev. 1995, 95, 1115-1133.
18. (d) Sellmann, D.; Sutter, J. Acc. Chem. Res. 1997, 30, 460-469.
19. (e) Malinak, S. M.; Coucouvanis, D. Prog. Inorg. Chem. 2001, 49, 599-662.
20. (a) Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 829.
21. (b) Patai, S., Ed. The Chemistry of Hydrazo, Azo, and Azoxy Groups; Wiley: New York, 1975.
22. (a) Haymore, B. L.; Ibers, J. A. Inorg. Chem. 1975, 14, 2784-2795.
23. (b) Laing, K. R.; Robinson, S. D.; Uttley, M. F. J. Chem. Soc., Chem. Commun. 1973, 176-177.
24. (a) Parshall, G. W. J. Am. Chem. Soc. 1967, 89, 1822-1826.
25. (b) Schrock, R. R.; Classman, T. E.; Vale, M. G. J. Am. Chem. Soc. 1991, 113, 725-726.
26. (c) Albertin, G.; Antoniutti, S.; Giorgi, M. T. Eur. J. Inorg. Chem. 2003, 2855-2866.
27. Smith, M. R., III; Keys, R. L.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1989, 111, 8312-8314.
28. (a) Albertin, G.; Antoniutti, S.; Pelizzi, G.; Vitali, F.; Bordignon, E. Inorg. Chem. 1988, 27, 829-835.
29. (b) Albertin, G.; Antoniutti, S.; Bacchi, A.; Bordignon, E.; Pelizzi, G.; Ugo, P. Inorg. Chem. 1996, 35, 6245-6253.
30. (c) Albertin, G.; Antoniutti, S.; Bacchi, A.; Bordignon, E.; Dolcetti, P. M.; Pelizzi, G. J. Chem. Soc., Dalton Trans. 1997, 4435-4444.
31. (d) Albertin, G.; Antoniutti, S.; Bacchi, A.; Bergamo, M.; Bordignon, E.; Pelizzi, G. Inorg. Chem. 1998, 37, 479-489.
32. (e) Albertin, G.; Antoniutti, S.; Bacchi, A.; Boato, M.; Pelizzi, G. J. Chem. Soc., Dalton Trans. 2002, 3313-3320.
33. (a) Albertin, G.; Antoniutti, S.; Bacchi, A.; Ballico, G. B.; Bordignon, E.; Pelizzi, G.; Ranieri, M.; Ugo, P. Inorg. Chem. 2000, 39, 3265-3279.
34. (b) Albertin, G.; Antoniutti, S.; Bordignon, E.; Perinello, G. J. Organomet. Chem. 2001, 625, 217-230.
35. (c) Albertin, G.; Antoniutti, S.; Bacchi, A.; Bordignon, E.; Giorgi, M. T.; Pelizzi, G. Angew. Chem., Int. Ed. 2002, 41, 2192-2194.
36. Rabinowitz, R.; Pellon, J. J. Org. Chem. 1961, 26, 4623-4626.
37. Vogel, A. I. Practical Organic Chemistry, 3rd ed.; Longmans, Green and Co.: New York, 1956.
38. Nachbaur, E.; Leiseder, G. Monatsh. Chem. 1971, 102, 1718-1723.
39. Balacco, G. J. Chem. Inf. Comput. Sci. 1994, 34, 1235-1241.
40. Peet, W. G.; Gerlach, D. H. Inorg. Synth. 1974, 15, 38-42.
41. Gerlach, D. H.; Peet, W. G.; Muetterties, E. L. J. Am. Chem. Soc. 1972, 94, 4545-4549.
42. Albertin, G.; Antoniutti, S.; Bordignon, E. J. Chem. Soc., Dalton Trans. 1989, 2353-2358.
43. Amendola, P.; Antoniutti, S.; Albertin, G.; Bordignon, E. Inorg. Chem. 1990, 29, 318-324.
44. (a) SAINT: SAX, Area Detector Integration; Siemens Analytical Instruments INC.: Madison, WI, Bruker AXS Copyright 1997-1999.
45. (b) Sheldrick, G. SADABS: Siemens Area Detector Absorption Correction Software; University of Göttingen: Göttingen, Germany, 1996.
46. Altomare, A.; Burla, M. C.; Cavalli, M.; Cascarano, G.; Giacovazzo, C.; Gagliardi, A.; Moliterni, A. G.; Polidori, G.; Spagna, R. Sir97: A New Program for Solving and Refining Crystal Structures; Istituto di Ricerca per lo Sviluppo di Metodologie Cristallografiche CNR: Bari, Italy, 1997.
47. Sheldrick, G. Shelxl97. Program for structure refinement; University of Göttingen: Göttingen, Germany, 1997.
48. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
49. (a) Allen, F. H.; Kennard, O.; Taylor, R. Acc. Chem. Res. 1983, 16, 146-153.
50. (b) Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389-397.
51. For reactions of hydride complexes with Brønsted acids, see: Kubas, G. J. Metal Dihydrogen and σ-Bond Complexes; Kluwer Academic: New York, 2001, and references therein.
52. 2+ intermediate is also plausible.
53. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122.
54. (a) Albertin, G.; Antoniutti, S.; Bortoluzzi, M. Inorg. Chem. 2004, 43, 1328-1335.
55. (b) Albertin, G.; Antoniutti, S.; Pizzol, S. J. Organomet. Chem. 2004, 689, 1639-1647.
56. (a) Nolte, M. J.; Singleton, E. J. Chem. Soc., Dalton Trans. 1974, 2406-2410.
57. (b) Day, V. W.; Everspacher, T. A.; Klemperer, W. G.; Planalp, R. P.; Schiller, P. W.; Yagasaki, A.; Zhong, B. Inorg. Chem. 1993, 32, 1629-1637.
58. 2 intermediate was also proposed, but only methane was detected: Ackermann, M. N.; Ellenson, J. L.; Robison, D. H. J. Am. Chem. Soc. 1968, 90, 7173-7174.
59. Heaton, B. T.; Jacob, C.; Monks, G. L.; Hursthouse, M. B.; Ghatak, I.; Somerville, R. G.; Heggie, W.; Page, P. R.; Villax, I. J. Chem. Soc., Dalton Trans. 1996, 61-67.
60. (a) Ashworth, T. V.; Singleton, E.; Hough, J. J. J. Chem. Soc., Dalton Trans. 1977, 1809-1815.
61. (b) Oosthuizen, H. E.; Singleton, T.; Fields, J. S.; Van Niekerk, G. G. J. Organomet. Chem. 1985, 279, 433-446.
62. (a) McCleverty, J. A.; Rae, A. E.; Wolochowicz, I.; Bailey, N. A.; Smith, J. M. A. J. Chem. Soc., Dalton Trans. 1983, 71-80.
63. (b) Sellmann, D.; Kern, W.; Pohlmann, G.; Knoch, F.; Moll, M. Inorg. Chim. Acta 1991, 185, 155-162.
64. (c) Chatt, J.; Dilworth, J. R.; Dahlstrom, P. L.; Zubieta, J. J. Chem. Soc., Chem. Commun. 1980, 786-787.
65. (d) Glassman, T. E.; Vale, M. G.; Schrock, R. R. J. Am. Chem. Soc. 1992, 114, 8098-8109.
66. (a) Nicholson, T.; Zubieta, J. J. Chem. Soc., Chem. Commun. 1985, 367-368.
67. (b) Barrientos-Penna, C. F.; Gilchrist, A. B.; Klahn-Oliva, A. H.; Hanlan, A. J. L.; Sutton, D. Organometallics 1985, 4, 478-485.