Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3369-3372

  Wang, Bo ^a   Gu, Yanlong ^a   Luo, Cheng ^a   Yang, Tao ^a   Yang, Liming ^a   Suo, Jishuan ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Amide; Beckmann rearrangement; Green synthesis; Ketoxime; Sulfamic acid

Indexed keywords

ACETONITRILE; ACID; AMIDE; AMPHOLYTE; BASE; OXIME DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; BECKMANN REARRANGEMENT; CATALYST; CHEMICAL WASTE; COST EFFECTIVENESS ANALYSIS; LIQUID; METHODOLOGY; RECYCLING; SYNTHESIS;

EID: 1842788776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.017     Document Type: Article

References (24)

1. Gawley R.E. Org. React. 35:1988;1. and references cited therein.
2. Smith M.B., March J. Advanced Organic Chemistry. 5th ed. 2001;1415 John Wiley and Sons, New York. and references cited therein.
3. Arisawa M., Yamaguchi M. Org. Lett. 3:2001;311.
4. Kikugawa Y., Tsuji C., Miyazawa E., Sakamoto T. Tetrahedron Lett. 42:2001;2337.
5. Anilkumar R., Chandrasekhar S. Tetrahedron Lett. 41:2000;5427.
6. Sato H., Yoshioka H., Izumi Y. J. Mol. Catal. A: Chem. 149:1999;25.
7. Laurent A., Jacquault P., Di Martino J.L., Hamelin J. J. Chem. Soc., Chem. Commun. 1995;1101.
8. Thakur A.J., Boruah A., Prajapati D., Sandhu J.S. Synth. Commun. 30:2000;2105.
9. Luca L.D., Giacomelli G., Porcheddu A. J. Org. Chem. 67:2002;6272.
10. Katritzky A.R., Monteux D.A., Tymoshenko D.O. Org. Lett. 4:1999;577.
11. Bosch A.I., Cruz P. de la, Diez-barra E., Loupy A., Langa F. Synlett. 1995;1259.
12. Kath H., Gläser R., Weitkamp J. Chem. Eng. Technol. 24(2):2001;150.
13. Peng J., Deng Y. Tetrahedron. Lett. 42:2001;403.
14. Ren R.X., Zueva L.D., Ou W. Tetrahedron. Lett. 42:2001;8441.
15. Jin T.S., Sun G., Li Y.W., Li T.S. Green Chem. 2002;255.
16. Li Y.Q. Chin. J. Int. Chem. 5(5):2003;40.
17. Jin T.S., Sun G., Li Y.W., Li T.S. J. Chem. Res., Synop. 1:2003;30.
18. Wang B., Yang L.M., Suo J.S. Synth. Commun. 33:2003;3929.
19. Wang, B.; Gu, Y. L.; Yang, L. M.; Suo, J. S. Catal. Lett. 2003 (in press).
20. Wang B., Yang L.M., Suo J.S. Tetrahedron Lett. 44:2003;5037.
21. Kanda F.A., King A.J. J. Am. Chem. Soc. 73:1951;2315.
22. Harbison G.S., Kye Y.-S., Penner G.H., Grandin M., Monette M. J. Phys. Chem. B. 106:2002;10285.
23. Donaruma L.G., Heldt W.Z. Org. React. 11:1960;1.
24. McCarty C.G. Patai S. Chemistry of Carbon-Nitrogen Double Bond. 1970;408 Wiley, New York.