Ceric ammonium nitrate (CAN) as oxidizing or nitrating reagent for organic reactions in ionic liquids

Tetrahedron Letters

Volumn 50, Issue 32, 2009, Pages 4582-4586

  Deleersnyder, Karen ^a   Schaltin, Stijn ^a   Fransaer, Jan ^a   Binnemans, Koen ^a   Parac Vogt, Tatjana N ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYL 3 METHYLIMIDAZOLIUM TRIFLATE; 2 METHYLNAPHTHALENE; AMMONIUM NITRATE; CERIC AMMONIUM NITRATE; CERIUM; IONIC LIQUID; NAPHTHALENE; OXIDIZING AGENT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ELECTROCHEMICAL ANALYSIS; NITRATION; OXIDATION; REGENERATION; WATER CONTENT;

EID: 67449088255     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.093     Document Type: Article

References (44)

1. Ho T.L. Synthesis (1973) 347-354
2. Molander G.A. Chem. Rev. 92 (1992) 29-68
3. Nair V., Balagopal L., Rajan R., and Mathew J. Acc. Chem. Res. 37 (2004) 21-30
4. Steel P.G. J. Chem. Soc., Perkin Trans. 1 (2001) 2727-2751
5. Nair V., and Deepthi A. Chem. Rev. 107 (2007) 1862-1891
6. Binnemans K. Applications of Tetravalent Cerium Compounds. In: Gschneidner Jr. K.A., Bünzli J.-C.G., and Pecharsky V.K. (Eds). Handbook on the Physics and Chemistry of Rare Earths Vol. 36, Chapter 229 (2006), Elsevier, Amsterdam 281-392
7. Jih R.H., and King K.Y. Curr. Sci. 81 (2001) 1043-1053
8. Trahanovsky W.S., Young L.B., and Brown G.L. J. Org. Chem. 32 (1967) 3865-3868
9. Trahanovsky W.S., and Young L.B.J. Org. Chem. 31 (1966) 2033-2035
10. Dziegiec J. Polish J. Chem. 59 (1985) 991-1000
11. Singh V., Sapehiyia V., and Kad G.L. Synthesis (2003) 198-200
12. Fischer A., and Henderson G.N. Synthesis (1985) 641-642
13. Chawla H.M., and Mittal R.S. Synthesis (1985) 70-72
14. Dincturk S., and Ridd J.H. J. Chem. Soc., Perkin Trans. 2 (1982) 965-969
15. Sarac A.S. Prog. Polym. Sci. 24 (1999) 1149-1204
16. Marko I.E., Ates A., Gautier A., Leroy B., Plancher J.M., Quesnel Y., and Vanherck J.C. Angew. Chem., Int. Ed. 38 (1999) 3207-3209
17. Maulide N., Vanherck J.C., Gautier A., and Marko I.E. Acc. Chem. Res. 40 (2007) 381-392
18. Christoffers J., Werner T., and Rossle M. Catal. Today 121 (2007) 22-26
19. Rossle M., Werner T., Frey W., and Christoffers J. Eur. J. Org. Chem. (2005) 5031-5038
20. Ganin E., and Amer I. Synth. Commun. 25 (1995) 3149-3154
21. Auty K., Gilbert B.C., Thomas C.B., Brown S.W., Jones C.W., and Sanderson W.R. J. Mol. Catal. A. 117 (1997) 279-287
22. Kreh R.P., Spotnitz R.M., and Lunsquist J.T. J. Org. Chem. 54 (1989) 1526-1531
23. Raju T., and Basha C.A. Chem. Eng. J. 114 (2005) 55-65
24. Carrijo R.M.C., and Romero J.R. Quim. Nov. 23 (2000) 331-337
25. Vijayabarathi T., Srinivasan R.K., and Noel M. Bull. Electrochem. 14 (1998) 279-282
26. Welton T. Chem. Rev. 99 (1999) 2071-2083
27. Dupont J., de Souza R.F., and Suarez P.A.Z. Chem. Rev. 102 (2002) 3667-3691
28. Parvulescu V.I., and Hardacre C. Chem. Rev. 107 (2007) 2615-2665
29. Wasserscheid P., and Keim W. Angew. Chem., Int. Ed. 39 (2000) 3773-3789
30. Wasserscheid P., and Welton T. Ionic Liquids in Synthesis (2002), Wiley-VCH, Weinheim
31. Chowdhury S., Mohan R.S., and Scott J.L. Tetrahedron 63 (2007) 2363-2389
32. Binnemans K. Chem. Rev. 107 (2007) 2592-2614
33. Bar G., Bini F., and Parsons A.F. Synth. Commun. 33 (2003) 213-222
34. Mehdi H., Bodor A., Lantos D., Horvath I.T., De Vos D.E., and Binnemans K.J. Org. Chem. 72 (2007) 517-524
35. Bonhôte P., Dias A.-P., Papageorgiou N., Kalyanasundaram K., and Grätzel M. Inorg. Chem. 35 (1996) 1168-1178
36. Bhatt M.V., and Periasamy M. J. Chem. Soc., Perkin Trans. 2 (1993) 1811-1814
37. Mellor J.M., Mittoo S., Parkes R., and Millar R.W. Tetrahedron 56 (2000) 8019-8024
38. Sheldon R.A. Top. Curr. Chem. 164 (1993) 21-43
39. Bohle A., Schubert A., Sun Y., and Thiel W.R. Adv. Synth. Catal. 348 (2006) 1011-1015
40. Yamazaki S. Tetrahedron Lett. 42 (2001) 3355-3357
41. 4, which also removed traces of ionic liquid that would contaminate the injection system and/or the column of the gas chromatograph. The resulting sample was diluted with acetone and analyzed by gas chromatography. Similar experiments were performed with a CAN:substrate ratio of 1:1 instead of the above mentioned 6:1 ratio. In this case the amount of CAN used was 1 mmol (548 mg), with the other experimental conditions left unchanged.
42. 2.
43. McEwen A.B., Ngo H.L., LeCompte K., and Goldman J.L. J. Electrochem. Soc. 6 (1999) 1687-1695
44. Earle M.J., Katdare S.P., and Seddon K.R. Org. Lett. 6 (2004) 707-710