Kinetics and selectivity of the copper-catalysed oxidative coupling of 4-(2',6'-dimethylphenoxy)-2,6-dimethylphenol

Journal of Molecular Catalysis A: Chemical

Volumn 140, Issue 3, 1999, Pages 241-253

  Baesjou, Patrick J ^a   Driessen, Willem L ^a   Challa, Ger ^b   Reedijk, Jan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Dimer; Dioxygen uptake; Homogeneous copper catalysis; Michaelis Menten; N Methylimidazole; Phenol oxidation; Reaction mechanism

Indexed keywords

4 (2',6' DIMETHYLPHENOXY) 2,6 DIMETHYLPHENOL; COPPER; IMIDAZOLE DERIVATIVE; OXYGEN; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MICHAELIS MENTEN KINETICS; OXIDATION; SYNTHESIS;

EID: 0033597396     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(98)00240-4     Document Type: Article

References (38)

1. Hay A.S., Stafford H.S., Endres G.F., Eustance J.W. J. Am. Chem. Soc. 81:1959;6335.
2. A.S. Hay, P. Shenian, A.C. Gowan, P.F. Erhardt, W.R. Haaf, J.E. Theberge, in: N.M. Bikales (Ed.), Encycl. Polym. Sci. and Techn., Vol. 10, Wiley, New York, 1969, p. 92.
3. D. Aycock, V. Abolins, D.M. White, in: H.F. Mark (Ed.), Encycl. Polym. Sci. and Eng., Vol. 13, 2nd edn., Wiley, New York, 1988, p. 1.
4. P.D. McDonald, G.A. Hamilton, in: W.S. Trahanovsky (Ed.), Oxidation in Organic Chemistry, Vol. 5B, Academic Press, New York, 1973, p. 97.
5. Hay A.S. J. Polym. Sci. 58:1962;581.
6. H.L. Finkbeiner, A.S. Hay, D.M. White, in: C.E. Schildknecht (Ed.), Polymerization Processes, Vol. XXIV, Wiley, New York, 1977, p. 537.
7. Kresta J., Tkác A., Prikryl R., Malik L. J. Elastoplast. 5:1973;20.
8. Kresta J., Tkác A., Prikryl R., Malik L. Makromol. Chem. 176:1975;157.
9. F.J. Viersen, PhD Thesis, Groningen University, 1988.
10. Viersen F.J., Challa G., Reedijk J. Polymer. 31:1990;1368.
11. W. Chen, PhD Thesis, Groningen University, 1991.
12. Challa G., Chen W., Reedijk J. Makromol. Chem., Macromol. Symp. 59:1992;59.
13. Baesjou P.J., Driessen W.L., Challa G., Reedijk J. J. Mol. Catal. A: Chem. 110:1996;195.
14. Baesjou P.J., Driessen W.L., Challa G., Reedijk J. J. Mol. Catal. A: Chem. 135:1998;273.
15. A.S. Hay, U.S. Patent 3,306,874, 1967.
16. J. McMurry, Organic Chemistry, Brooks/Cole, Monterey, CA, 1984, p. 1167.
17. E. Tsuchida, K. Yamamoto, in: J. Reedijk (Ed.), Bioinorganic Catalysis, Marcel Dekker, New York, 1993, p. 29.
18. Cooper G.D., Bennet J.G. J. Org. Chem. 37:1972;441.
19. Endres G.F., Kwiatek J. J. Polym. Sci. 58:1962;593.
20. Viersen F.J., Renkema J., Challa G., Reedijk J. J. Polym. Sci. Polym. Chem. 30:1992;901.
21. A.I. Vogel, A Textbook of Practical Organic Chemistry Including Quantitative Organic Analysis, 3rd edn., Longman, London, 1956, p. 190.
22. Tullemans A.H.J., Bouwman E., de Graaff R.A.G., Driessen W.L., Reedijk J. Recl. Trav. Chim. Pays-Bas. 109:1990;70.
23. P.J. Baesjou, PhD Thesis Leiden University, 1997.
24. Baesjou P.J., Driessen W.L., Challa G., Reedijk J. J. Am. Chem. Soc. 119:1997;12590.
25. Ullmann F. Berichte. 37:1904;853.
26. van Heyningen E. J. Org. Chem. 26:1961;3850.
27. Moroz A.A., Shvartsberg M.S. Russ. Chem. Rev. 43:1974;679.
28. Bruice T.C., Kharasch N., Winzler R.J. J. Org. Chem. 18:1953;83.
29. D.A. Skoog, D.M. West, Fundamentals of Analytical Chemistry, Holt, Rinehart and Winston, New York, 1963, p. 786.
30. P.W. Atkins, Physical Chemistry, 3rd edn., Oxford University Press, Oxford, 1986, p. 857.
31. F.M. Konrad, in: N.M. Bikales (Ed.), Encycl. Polym. Sci. and Techn., Vol. 10, Wiley, New York, 1969, p. 73.
32. Cooper G.D., Blanchard H.S., Endres G.F., Finkbeiner H. J. Am. Chem. Soc. 87:1965;3996.
33. Cooper G.D., Gilbert A.R., Finkbeiner H. Polymer Preprints. 7:1966;166.
34. Mijs W.J., van Lohuizen O.E., Bussink J., Vollbracht L. Tetrahedron. 23:1967;2253.
35. P.J. Baesjou, W.L. Driessen, G. Challa, J. Reedijk, Macromolecules, Manuscript in Preparation, 1998.
36. Viersen F.J., Challa G., Reedijk J. Polymer. 31:1990;1361.
37. Tsuchida E., Kaneko M., Nishide H. Makromol. Chem. 151:1972;221.
38. Chen W., Challa G. Eur. Polym. J. 26:1990;1211.