Cyanuric chloride catalyzed Beckmann rearrangement of ketoximes in biodegradable ionic liquids

Tetrahedron

Volumn 68, Issue 7, 2012, Pages 1947-1950

  Maia, Angelamaria ^a   Albanese, Domenico C M ^b   Landini, Dario ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Amides; Beckmann rearrangement; Biodegradable ionic liquids; Cyanuric chloride; Organocatalysis

Indexed keywords

1 HEXYL 3 METHYLIMIDAZOLIUM; 2,4,6 TRICHLO [1,3,5] TRIAZINE; 3 METHYL 1 (BUTOXYCARBONYLMETHYL) IMIDAZOLIUM; ALIPHATIC COMPOUND; AROMATIC COMPOUND; CYANURIC CHLORIDE; CYCLOALIPHATIC SUBSTRATE; ESTER; IMIDAZOLIUM; IONIC LIQUID; KETOXIME DERIVATIVE; TRIAZINE; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; BIODEGRADABILITY; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 84856390888     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.051     Document Type: Article

References (28)

1. R.E. Gawly Org. React. 35 1988 1 420 and references therein
2. M.B. Smith, and J. March Advanced Organic Chemistry 5th ed. 2001 John Wiley and Sons New York, NY page 1415 and references therein
3. A.R. Sardarian, Z. Shahsavari-Fard, H.R. Shahsavari, and Z. Ebrahimi Tetrahedron Lett. 48 2007 2639 2643
4. R.X. Ren, L.D. Zueva, and W. Ou Tetrahedron Lett. 42 2001 8441 8443
5. J. Peng, and Y. Deng Tetrahedron Lett. 42 2001 403 405
6. S. Guo, Z. Du, S. Zhang, D. Li, Z. Li, and Y. Deng Green Chem. 8 2006 296 300 and references therein
7. L.D. Yadav, and G.V.P. Srivastava Tetrahedron Lett. 51 2010 739 743
8. R.D. Rogers, and K.R. Seddon Ionic Liquids III A: Fundamentals, Progress, Challenges and Opportunities-Properties and Structure 2005 American Chemical Society Washington DC
9. R.D. Rogers, and K.R. Seddon Ionic Liquids III B: Fundamentals, Progress, Challenges and Opportunities-Transformations and Processes 2005 American Chemical Society Washington DC
10. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2nd ed. 2008 Wiley-VCH Weinheim
11. N.V. Plechkova, and K.R. Seddon Chem. Soc. Rev. 37 2008 123 150
12. F.M. Kerton Alternative Solvents for Green Chemistry, RSC Green Chemistry Series 2009 The Royal Society of Chemistry Cambridge
13. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
14. A. Maia Mini-Rev. Org. Chem. 8 2011 178 185
15. D. Coleman, and N. Gathergood Chem. Soc. Rev. 39 2010 600 637
16. R.S. Boethling, E. Sommer, and D. Di Fiore Chem. Rev. 107 2007 2207 2227
17. N. Gathergood, and P.J. Scammells Aust. J. Chem. 55 2002 557 560
18. N. Gathergood, M.T. Garcia, and P.J. Scammells Green Chem. 6 2004 166 175
19. M.T. Garcia, N. Gathergood, and P.J. Scammells Green Chem. 7 2005 9 14
20. S. Morrissey, I. Beadham, and N. Gathergood Green Chem. 11 2009 466 474
21. J.R. Harjani, R.D. Singer, M.T. Garcia, and P.J. Scammells Green Chem. 11 2009 83 90
22. C. Betti, D. Landini, A. Maia, and M. Pasi Synlett 2008 908 910 and references therein
23. S. Morrissey, B. Pegot, D. Coleman, M.T. Garcia, D. Ferguson, B. Quilty, and N. Gathergood Green Chem. 11 2009 475 483
24. Y. Furuya, K. Ishihara, and H. Yamamoto J. Am. Chem. Soc. 127 2005 11240 11241
25. M. Zhu, C. Cha, W.-P. Deng, and X.-X. Shi Tetrahedron Lett. 47 2006 4861 4863
26. 2, filtered on Celite, and reused after removal of the organic solvent under vacuum.
27. H.-J. Pi, J.-D. Dong, N. An, W. Du, and W.-P. Deng Tetrahedron 65 2009 7790 7793
28. L. De Luca, G. Giacomelli, and A. Porcheddu J. Org. Chem. 67 2002 6272 6274