Alkene oxidation by a platinum oxo complex and isolation of a platinaoxetane

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10522-10523

  Szuromi, Endre ^a   Shan, Hui ^a   Sharp, Paul R ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; ALKENE; ETHYLENE; OXYGEN 17; PLATINAOXETANE; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0041854727     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036496c     Document Type: Article

References (31)

1. Jørgensen, K. A. Chem. Rev. 1989, 89, 431-458.
2. Hosokawa, T.; Takano, M.; Murahashi, S. I. J. Am. Chem. Soc. 1996, 118, 3990-3991.
3. Mimoun, H.; Perez Machirant, M. M.; Seree de Roch, I. J. Am. Chem. Soc. 1978, 100, 5437-5444.
4. Bocquet, M.-L.; Michaelides, A.; Loffreda, D.; Sautet, P.; Alavi, A.; King, D. A. J. Am. Chem. Soc. 2003, 125, 5620-5621.
5. Linic, S.; Barteau, M. A. J. Am. Chem. Soc. 2003, 125, 4034-4035.
6. (a) Calhorda, M. J.; Lopes, P. E. M.; Friend, C. M. J. Mol. Catal. A: Chem. 1995, 97, 157-171.
7. (b) Guo, X.-C.; Madix, R. J. J. Am. Chem. Soc. 1995, 117, 5523-5530.
8. (c) Madix, R. J.; Roberts, J. T. In Surface Reactions; Madix, R. J., Ed. ; Springer-Verlag: New York, 1994; pp 5-53.
9. Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483-1506.
10. Klein, D. P.; Hayes, J. C.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 3704-3707.
11. Metallaoxetanes have been obtained from the reaction of alkene complexes with dioxygen or hydrogen peroxide: (a) Day, V. W.; Klemperer, W. G.; Lockledge, S. P.; Main, D. J. J. Am. Chem. Soc. 1990, 112, 2031-2033. (b) de Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; de Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem., Eur. J. 2000, 6, 298-312. (c) Flood, T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino, T. E. Chem. Commun. 2000, 1681-1682.
12. Metallaoxetanes have been obtained from the reaction of alkene complexes with dioxygen or hydrogen peroxide: (a) Day, V. W.; Klemperer, W. G.; Lockledge, S. P.; Main, D. J. J. Am. Chem. Soc. 1990, 112, 2031-2033. (b) de Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; de Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem., Eur. J. 2000, 6, 298-312. (c) Flood, T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino, T. E. Chem. Commun. 2000, 1681-1682.
13. Metallaoxetanes have been obtained from the reaction of alkene complexes with dioxygen or hydrogen peroxide: (a) Day, V. W.; Klemperer, W. G.; Lockledge, S. P.; Main, D. J. J. Am. Chem. Soc. 1990, 112, 2031-2033. (b) de Bruin, B.; Boerakker, M. J.; Verhagen, J. A. W.; de Gelder, R.; Smits, J. M. M.; Gal, A. W. Chem., Eur. J. 2000, 6, 298-312. (c) Flood, T. C.; Iimura, M.; Perotti, J. M.; Rheingold, A. L.; Concolino, T. E. Chem. Commun. 2000, 1681-1682.
14. Shan, H.; James, A. J.; Sharp, P. R. Inorg. Chem. 1998, 37, 5727-5732.
15. 3) is described therein: Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411-428. We have prepared 2 analogously and report its NMR properties in Supporting Information.
16. Boag, N. M.; Green, M.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1980, 1200-1207.
17. Examples of formylmethyl complexes: (a) Tsutsui, M.; Ori, M.; Francis, J. J. Am. Chem. Soc. 1972, 94, 1414-1415.
18. (b) Hillis, J.; Francis, J.; Ori, M.; Tsutsui, M. J. Am. Chem. Soc. 1974, 96, 4800-4804.
19. (c) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774.
20. (d) Wu, J.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 7628-7630.
21. (e) Woerpel, K. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 7888.
22. (f) Ritter, J. C. M.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 2580-2581.
23. (g) Matsumoto, K.; Nagai, Y.; Matsunami, J.; Mizuno, K.; Abe, T.; Somazawa, R.; Kinoshita, J.; Shimura, H. J. Am. Chem. Soc. 1998, 120, 2900-2907.
24. (h) De Bruin, B.; Peters, T. P. J.; Thewissen, S.; Blok, A. N. J.; Wilting, J. B. M.; De Gelder, R.; Smits, J. M. M.; Gal, A. W. Angew. Chem. Int. Ed. 2002, 41, 2135-2138.
25. (i) Krom, M.; Coumans, R. G. E.; Smits, J. M. M.; Gal, A. W. Angew. Chem. Int. Ed. 2002, 41, 575-579.
26. Examples of oxaallyl complexes: (a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022-2039.
27. (b) Lemke, F. R.; Kubiak, C. P. J. Organomet. Chem. 1989, 373, 391-400.
28. (c) Slough, G. A.; Hayashi, R.; Ashbaugh, J. R.; Shamblin, S. L.; Aukamp, A. M. Organometallics 1994, 13, 890-898.
29. (d) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058.
30. Padilla-Martinez, I. I.; Poveda, M. L.; Carmona, E.; Monge, M. A.; Ruiz-Valero, C. Organometallics 2002, 21, 93-104.
31. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley and Sons: New York, 2001.