An ionic liquid based on a cyclic guanidinium cation is an efficient medium for the selective oxidation of benzyl alcohols

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 2013-2015

  Xie, Haibo ^a   Zhang, Suobo ^a   Duan, Haifeng ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

Author keywords

Ionic liquids; Oxidation of benzyl alcohols; Phase transfer catalyst

Indexed keywords

BENZALDEHYDE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CATION; ETHER; GUANIDINE DERIVATIVE; HYPOCHLORITE SODIUM; ION; OXIDIZING AGENT; SOLVENT;

ALCOHOL OXIDATION; ARTICLE; CATALYST; EXTRACTION; LIQUID; OXIDATION; RECYCLING; ROOM TEMPERATURE;

EID: 1242316295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.141     Document Type: Article

References (32)

1. Welton T. Chem. Rev. 99:1999;2071-2083.
2. Wasserscheid P., Keim W. Angew. Chem., Int. Ed. 39:2000;3772-3789.
3. Seldon R.A. Chem. Commun. 2001;2399-2407.
4. Dupont J., De Souza R.F., Suarez P.A.Z. Chem. Rev. 102:2002;3667-3692.
5. Boon J.A., Levisky J.A., Pflug J.L., Wilkes J.S. J. Org. Chem. 51:1986;480-483.
6. Brown R.A., Pollet P., McKoon E., Eckert C.A., Liotta C.L., Jessop P.G. J. Am. Chem. Soc. 123:2001;1254-1255.
7. Chauvin Y., Mussmann L., Olivier H. Angew. Chem., Int. Ed. Engl. 34:1995;2698-2700.
8. Favre F., Olivier-Bourbigou H., Commereuc D., Saussine L. Chem. Commun. 2001;1360-1361.
9. Mattews C.J., Smith P.J., Welton T. Chem. Commun. 2000;1249-1250.
10. Nishimura T., Ohe K., Onoue T., Uemura S. J. Org. Chem. 64:1999;6750-6755.
11. Nishimura T., Ohe K., Uemura S. J. Am. Chem. Soc. 121:1999;2645-2646.
12. Hallman K., Moberg C. Adv. Synth. Catal. 343:2001;260-263.
13. Bortolo R., Bianchi D., D' Aloisio R., Querci C., Ricci M. J. Mol. Catal. A. Chem. 153:2000;25-29.
14. Markó I.E., Giles P.R., Tsukazaki M., Brown S.M., Urch C.J. Science. 274:1996;2044-2046.
15. Iwahama T., Yoshino Y., Keitoku T., Sakaguchi S., Ishii Y. J. Org. Chem. 65:2000;6502-6507.
16. Markó I.E., Giles P.R., Tsukazaki M., Chellé-Regnaut I., Urch C.J., Brown S.M. J. Am. Chem. Soc. 119:1997;12661-12662.
17. Dijksman A., Marino-Gonzalez A., Mairata I Payeras A., Arends I.W.C.E., Sheldon R.A. J. Am. Chem. Soc. 123:2001;6826-6833.
18. Seddon K.R., Stark A. Green Chem. 4:2002;119-123.
19. Farmer V., Welton T. Green Chem. 4:2002;97-102.
20. Ansai I.A., Gree R. Org. Lett. 4:2002;1507-1509.
21. Ley S.V., Ramarao C., Smith M.D. Chem. Commun. 2001;2278-2279.
22. Wolfson A., Wuyts S., De Vos D.E., Vankelecom I.F.J., Jacobs P.A. Tetrahedron Lett. 43:2002;8107-8110.
23. Lee G.A., Freedman H.H. Tetrahedron Lett. 20:1976;1641-1644.
24. Abramovici S., Neumann R., Sasson Y. J. Mol. Catal. 29:1985;291-297.
25. Reddy Ch.V., Mashsh M., Raju P.V.K., Reddy V.V.N. Syn. Commun. 2002;2797-2802.
26. Abramovici S., Neumann R., Sasson Y. J. Mol. Catal. 29:1985;299-303.
27. Do J.S., Chou T.C. Ind. Eng. Chem. Res. 29:1990;1095-1103.
28. Grigoropoulou G., Clark J.H., Hall D.W., Scott K. Chem. Commun. 2001;547-548.
29. Suarez P.A.Z., Dullius J.E.L., Einloft S., de Souza R.F., Dupont J. Polyhedron. 15:1996;1217-1219.
30. US Patent 5,132,423.
31. 3-N).
32. Typical procedure for oxidation: RTIL(10 mL) was added to a 250 mL three-necked, round-bottomed flask containing benzyl alcohol (1.08 g 10 mmol), then 25 g 10% aqueous sodium hypochlorite (pH=8-9) was added dropwise under vigorous mechanical stirring. The biphasic mixture was stirred for one hour under ambient conditions ( T∼25°C, atmospheric pressure) and then the mixture was extracted with diethyl ether (3 × 20 mL), after which the diethyl ether was evaporated and the yield was checked by gas chromatography with an internal standard.