Rhodium-catalyzed Beckmann rearrangement

Organic Letters

Volumn 3, Issue 2, 2001, Pages 311-312

  Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000045680     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006951z     Document Type: Article

References (16)

1. Gawly, R. E. Org. React. 1988, 35, 1 and references therein.
2. Izumi, Y.; Sato, S.; Urabe, K. Chem. Lett. 1983, 1649.
3. Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. J. Am. Chem. Soc. 2000, 122, 1908. Sato, O.; Ikushima, Y.; Yokoyama, T. J. Org. Chem. 1998, 63, 9100.
4. Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. J. Am. Chem. Soc. 2000, 122, 1908. Sato, O.; Ikushima, Y.; Yokoyama, T. J. Org. Chem. 1998, 63, 9100.
5. Izumi, Y. Chem. Lett. 1990, 2171.
6. Kusama, H.; Yamashita, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 373. Narasaka, K.; Kusama, H.; Yamashita, Y.; Sato, H. Chem. Lett. 1993, 489.
7. Kusama, H.; Yamashita, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 373. Narasaka, K.; Kusama, H.; Yamashita, Y.; Sato, H. Chem. Lett. 1993, 489.
8. Mukaiyama, T.; Harada, T. Chem. Lett. 1991, 1653. Harada, T.; Ohno, T.; Kobayashi, S.; Mukaiyama, T. Synthesis 1991, 1216.
9. Mukaiyama, T.; Harada, T. Chem. Lett. 1991, 1653. Harada, T.; Ohno, T.; Kobayashi, S.; Mukaiyama, T. Synthesis 1991, 1216.
10. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, in press.
11. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, in press.
12. 2 (0.5 mol %, 12.3 mg), tris(p-tolyl)phosphine (3 mol %, 45.7 mg), benzophenone oxime (5.0 mmol, 985 mg), and trifluoromethanesulfonic acid (5 mol %, 0.022 mL) in dichloroethane (4 mL) under an argon atmosphere, and the solution was heated at reflux for 3 h. Then, water was added, and the organic materials were extracted twice with ether. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography to give benzanilide (916 mg, 93%).
13. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Ferreira, C. M. P.; Guedes de Silva, M. F. C.; Kukushkin, V. Y.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 325. Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem. 1990, 398, 299. Hosokawa, T.; Shimo, N.; Maeda, K.; Sonoda, A.; Murahashi, S. Tetrahedron Lett. 1976, 383.
14. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Ferreira, C. M. P.; Guedes de Silva, M. F. C.; Kukushkin, V. Y.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 325. Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem. 1990, 398, 299. Hosokawa, T.; Shimo, N.; Maeda, K.; Sonoda, A.; Murahashi, S. Tetrahedron Lett. 1976, 383.
15. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Ferreira, C. M. P.; Guedes de Silva, M. F. C.; Kukushkin, V. Y.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 325. Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem. 1990, 398, 299. Hosokawa, T.; Shimo, N.; Maeda, K.; Sonoda, A.; Murahashi, S. Tetrahedron Lett. 1976, 383.
16. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Ferreira, C. M. P.; Guedes de Silva, M. F. C.; Kukushkin, V. Y.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 325. Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem. 1990, 398, 299. Hosokawa, T.; Shimo, N.; Maeda, K.; Sonoda, A.; Murahashi, S. Tetrahedron Lett. 1976, 383.