Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst

Journal of Organic Chemistry

Volumn 73, Issue 7, 2008, Pages 2894-2897

  Hashimoto, Masaharu ^a   Obora, Yasushi ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BECKMANN REARRANGEMENT; TRIPHOSPHAZENE CATALYST;

CATALYST ACTIVITY; NYLON POLYMERS; RAW MATERIALS;

KETONES;

1,3,5 TRIAZO 2,4,6 TRIPHOSPHORINE 2,2,4,4,6,6 CHLORIDE; BIOMATERIAL; CAPROLACTAM; CYCLODODECANONE OXIME; CYCLOHEXANONE DERIVATIVE; CYCLOHEXANONE OXIME; KETONE DERIVATIVE; LACTAM DERIVATIVE; LAUROLACTAM; NYLON; OXIME DERIVATIVE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; BIOTRANSFORMATION; CATALYST; CHEMICAL ENGINEERING; REACTION ANALYSIS;

EID: 41649115873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702277g     Document Type: Article

References (18)

1. (a) Luedeke, V. D. In Encyclopedia of Chemical Processing and Design; Mcketta, J. J., Ed.; Marcel Dekker: New York, 1978; pp 72-95.
2. (b) Rademacher, H. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Gerhartz, W., Ed.; Wiley: New York, 1987; Vol. A8, pp 201-203.
3. (c) Weber, J. N. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1990; Vol. 19, pp 500-501.
4. (d) Wessermel, K.; Arpe H.-J. Industrial Organic Chemistry, 4th ed.; Wiley-VCH: Weinheim, Germany, 2003; pp 239-266.
5. For recent examples of transition-metal-catalyzed Beckmann rearrangement of oximes, see: (a) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 3599.
6. (b) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 73.
7. (c) Park, S.; Choi, Y.; Han, H.; Yang, S. H.; Chang, S. Chem. Commun. 2003, 1936.
8. Fisher, W. B.; Crescentini, L. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Ed.; Wiley: New York, 1990; Vol. 4, pp 827-839.
9. (a) Takahashi, T.; Kai, T.; Nakao, E. Appl. Catal. A 2004, 262, 137.
10. (b) Forni, L.; Fornasari, G.; Giordano, G.; Lucarelli, C.; Katovic, A.; Trifirò, F.; Perri, C.; Nagy, J. B. Phys. Chem. Chem. Phys. 2004, 6, 1842 and references cited therein.
11. Furuya, Y.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 11240.
12. Hashimoto, M.; Sakaguchi, S.; Ishii, Y. Chem. Asian J. 2006, 1, 712.
13. Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Angew. Chem., Int. Ed. 2004, 43, 1120.
14. (a) Rosini, G.; Baccolini, G.; Cacchi, S. J. Org. Chem. 1973, 38, 1060.
15. (b) Trunbull, J. H. Chem. Ind. 1956, 350.
16. Katritzky, A. R.; Cai, C.; Singh, S. K. J. Org. Chem. 2006, 71, 3375.
17. Mazurkiewicz, R. Acta Chim. Hung. 1990, 127, 439;
18. Chem. Abstr. 1991, 114, 206 693.