Aerobic oxidation of 2,3,6-trimethylphenol to trimethyl-1,4-benzoquinone with copper(II) chloride as catalyst in ionic liquid and structure of the active species

Journal of the American Chemical Society

Volumn 126, Issue 31, 2004, Pages 9550-9551

  Sun, Hongjian ^a,b   Harms, Klaus ^a   Sundermeyer, Joerg ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; 2,3,6 TRIMETHYLPHENOL; COBALT COMPLEX; COPPER CHLORIDE; HYDROGEN PEROXIDE; IRON COMPLEX; TRIMETHYL 1,4 BENZOQUINONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CRYSTAL STRUCTURE; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY; SULFONATION;

BENZOQUINONES; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PHENOLS;

EID: 3543064755     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0391964     Document Type: Article

References (28)

1. Shimizu, M.; Orita, H.; Hayakawa, T.; Takehira, K. Tetrahedron Lett. 1989, 30, 471-474.
2. Asakawa, Y.; Matsuda, R.; Hashimoto, T. (Kuraray Co., Ltd.). Jp 5939847, 1984; Chem. Abstr. 1984, 101 130395x.
3. Sorokin, A. B.; Tuel, A. New J. Chem. 1999, 23, 473-476.
4. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidation of Organic Compounds: Academic Press: New York, 1981; p 373-381.
5. Brenner, W. (Hoffman-La Roche). German Patent 2,221,624, 1972.
6. Eur. Pat. Appl. (BASF AG). EP 475,272 A2, 1992.
7. Isshiki, T.; Yui, T.; Uno, H.; Abe, M. (Mitsubishi Gas Chemical Co.). Eur. Pat. 0,127,888, 1984.
8. (a) Takehira, K.; Shimizu, M.; Watanabe, Y.; Orita, H.; Hayakawa, T. J. Chem. Soc., Chem. Commun. 1989, 1705-1706.
9. (b) Takehira, K.; Shimizu, M.; Watanabe, Y.; Orita, H.; Hayakawa, T. Tetrahedron Lett. 1989, 30, 6691-6692.
10. (c) Shimizu, M.; Watanabe, Y.; Orita, H.; Hayakawa, T.; Takehira, K. Bull. Chem. Soc. Jpn. 1992, 65, 1522-1526.
11. Baiker, A.; Bodnar, Z.; Mallat, T. J. Mol. Catal. A 1996, 110, 55-63.
12. Takaki, K.; Shimasaki, Y.; Shishido, T.; Takehira, K. Bull. Chem. Soc. Jpn. 2002, 75, 311-317.
13. Meng, X.; Sun, Z.; Lin, S.; Yang, M.; Yang, X.; Sun, J.; Jiang, D.; Xiao, F.; Chen, S. Appl. Catal. A 2002, 236, 17-22.
14. Boon, J. A.; Levisky, J. A.; Pflug, J. L.; Wilkes, J. S. J. Org. Chem. 1986, 51, 480-483.
15. (a) Wasserscheid, P.; Keim, W. Angew. Chem. 2000, 112, 3926-3945; Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
16. (a) Wasserscheid, P.; Keim, W. Angew. Chem. 2000, 112, 3926-3945; Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
17. (b) Chauvin, Y.; Olivier-Bourbigou, H. CHEMTECH 1995, 25, 26-30.
18. (c) Sheldon, R. Chem. Commun. 2001, 2399-2407.
19. (d) Dupont, J.; Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 3667-3692.
20. (e) Gordon, C. M. Appl. Catal. A 2001, 222, 101-117.
21. (f) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157-189.
22. Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837-838.
23. Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507-1509.
24. (a) Belford, R.; Fenton, D. E.; Truter, M. R. J. Chem. Soc., Dalton Trans. 1972, 2345-2350.
25. (b) Harlow, R. L.; Simonsen, S. H. Acta Crystallogr. 1977, B33, 2784-2387.
26. (c) Bertrand, J. A.; Kelley, J. A. Inorg. Chem. 1969, 9, 1982-1985.
27. (d) Clegg, W.; Nicholson, J. R.; Collison, D.; Garner, C. D. Acta Crystallogr. 1988, C44, 453-461.
28. (e) Davies, G.; El-Shazly, M. F.; Rupich, M. W. J. Chem. Soc., Chem. Commun. 1978, 1045-1046.