Platinum(II)-catalyzed isomerization of alkoxycyclopropanes to alkylated ketones

Organometallics

Volumn 15, Issue 18, 1996, Pages 3902-3904

  Hoberg, John O ^b   Jennings, P W ^a  

^a MONTANA STATE UNIVERSITY   (United States)

^b NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000761411     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960157t     Document Type: Article

References (36)

1. For reviews see: (a) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (c) Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Bishop, K. C., III. Chem. Rev. 1976, 76, 461.
2. For reviews see: (a) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (c) Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Bishop, K. C., III. Chem. Rev. 1976, 76, 461.
3. For reviews see: (a) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (c) Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Bishop, K. C., III. Chem. Rev. 1976, 76, 461.
4. For reviews see: (a) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (c) Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Bishop, K. C., III. Chem. Rev. 1976, 76, 461.
5. For reviews see: (a) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (c) Puddephatt, R. J. Coord. Chem. Rev. 1980, 33, 149. (d) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (e) Bishop, K. C., III. Chem. Rev. 1976, 76, 461.
6. (a) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326.
7. (b) Parsons, E. I.; Jennings, P. W. Organometallics 1988, 7, 1435.
8. (c) Meijere, A. Angew. Chem., Int. Ed. Eng. 1979, 18, 809.
9. (d) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
10. (e) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296.
11. (a) Pellicciari, R.; Arenare, L.; Caprariis, P. D.; Natalini, B.; Marinozzi, M.; Galli, A. J. Chem. Soc., Perkin Trans. 1 1995, 1251.
12. (b) Lautens, M.; Ren, Y.; Delanghe, P.; Chiu, P.; Ma, S.; Colucci, J. Can. J. Chem. 1995, 73, 1251.
13. (c) Donaldson, W. A.; Stepuszek, D. J. J. Org. Chem. 1992, 57, 1309.
14. (d) Saigo, K.; Shimada, S.; Shibasaki, T.; Hasegawa, M. Chem. Lett. 1990, 1093.
15. (e) Saigo, K.; Shimada, S.; Hashimoto, Y.; Nagashima, T.; Hasegawa, M. Chem. Lett. 1990, 1101.
16. (f) Neilsen, W. D.; Larsen, R. D.; Jennings, P. W. J. Am. Chem. Soc. 1988, 110, 3307.
17. (g) Neilsen, W. D.; Larsen, R. D.; Jennings, P. W. J. Am. Chem. Soc. 1988, 110, 8657.
18. (h) Paquette, L. A. Chem. Rev. 1986, 86, 733.
19. (a) Stewart, F. F.; Neilsen, W. D.; Ekeland, R. E.; Larsen, R. D.; Jennings, P. W. Organometallics 1993, 12. 4585.
20. (b) Hoberg, J. O.; Jennings, P. W. Organometallics 1992, 11, 3452.
21. (c) Hoberg, J. O.; Jennings, P. W. Organometallics 1991, 10, 8.
22. (a) Parsons, E. J.; Jennings, P. W. J. Am. Chem. Soc. 1987, 109, 3973.
23. (b) Parsons, E. J.; Larsen, R. D.; Jennings, P. W. J. Am. Chem. Soc. 1985, 107, 1793.
24. (a) Irwin, W. J.; McQuillin, F. J. Tetrahedron Lett. 1968, 1937.
25. (b) Powell, K. G.; McQuillin, F. J. Tetrahedron Lett. 1971, 3313.
26. Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520. For additional related work see ref 4a.
27. Hoberg, J. O.; Larsen, R. D.; Jennings, P. W. Organometallics 1990, 9, 1334.
28. 4. See ref 3b and: (a) Ekeland, R. A.; Jennings, P. W. J. Organomet. Chem. 1985, 281, 397. (b) Hanks, T. W.; Ekeland, R. A.; Emerson, K.; Larsen, R. D.; Jenning, P. W. Organometallics 1987, 6, 28. (c) Hanks, T. W.; Jennings, P. W. J. Am. Chem. Soc. 1987, 109, 5023.
29. 4. See ref 3b and: (a) Ekeland, R. A.; Jennings, P. W. J. Organomet. Chem. 1985, 281, 397. (b) Hanks, T. W.; Ekeland, R. A.; Emerson, K.; Larsen, R. D.; Jenning, P. W. Organometallics 1987, 6, 28. (c) Hanks, T. W.; Jennings, P. W. J. Am. Chem. Soc. 1987, 109, 5023.
30. 4. See ref 3b and: (a) Ekeland, R. A.; Jennings, P. W. J. Organomet. Chem. 1985, 281, 397. (b) Hanks, T. W.; Ekeland, R. A.; Emerson, K.; Larsen, R. D.; Jenning, P. W. Organometallics 1987, 6, 28. (c) Hanks, T. W.; Jennings, P. W. J. Am. Chem. Soc. 1987, 109, 5023.
31. Reaction of 1-methoxybicyclo[4.1.0]heptane requires stoichiometric amounts of platinum implying the formation of a carbene type ligand.
32. Ikura, K.; Ryu, I.; Ogawa, A.; Sonoda, N.; Harada, S.; Kasai, N. Organometallics 1991, 10, 528. The platinum complex was established by X-ray crystallography: equation presented For additional evidence see: Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371.
33. Ikura, K.; Ryu, I.; Ogawa, A.; Sonoda, N.; Harada, S.; Kasai, N. Organometallics 1991, 10, 528. The platinum complex was established by X-ray crystallography: equation presented For additional evidence see: Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371.
34. (a) Ryu, I.; Aya, T.; Otani, S.; Murai, S.; Sonoda, N. J. Organomet. Chem. 1987, 327, 279.
35. (b) Ryu, I.; Murai, S.; Sonoda, N. Chem. Lett. 1976, 10, 1049.
36. (c) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354.