Ab initio calculations on 2,6-dimethylphenol and 4-(2,6- dimethylphenoxy)-2,6-dimethylphenol. Evidence of an important role for the phenoxonium cation in the copper-catalyzed oxidative phenol coupling reaction

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12590-12594

  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

[No Author keywords available]

Indexed keywords

CATION; COPPER; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; MOLECULAR INTERACTION; OXIDATION; POLYMERIZATION; SYNTHESIS;

EID: 0031585688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971612v     Document Type: Article

References (36)

1. Hay, A. S.; Stafford, H. S.; Endres, G. F.; Eustance, J. W. J. Am. Chem. Soc. 1959, 81, 6335-6336.
2. Systematic name: 4-(3,5-dimethyl-4-oxo-2,5-cyclohexadienylidene)-2,6-dimethyl-2,5- cyclohexadienone.
3. Mijs, W. J.; van Dijk, J. H.; Huysmans, W. G. B.; Westra, J. G. Tetrahedron 1969, 25, 4233-4240.
4. Hay, A. S.; Shenian, P.; Gowan, A. C.; Erhardt, P. F.; Haaf, W. R.; Theberge, J. E. In Encyclopedia of Polymer Science and Technology; Bikales, N. M., Ed.; Wiley & Sons: New York, 1969; Vol. 10, pp 92-111.
5. Aycock, D.; Abolins, V.; White, D. M. In Encyclopedia of Polymer Science and Engineering; Mark, H. F., Ed.; Wiley & Sons: New York, 1988; Vol. 13, pp 1-30.
6. Staffin, G. D.; Price, C. C. J. Am. Chem. Soc. 1960, 82, 3632-3634.
7. Tsuchida, E.; Kaneko, M.; Nishide, H. Makromol. Chem. 1972, 151, 221-234.
8. Price, C. C.; Nakaoka, K. Macromolecules 1971, 4, 363-369.
9. Roubaty, J. L.; Bréant, M.; Lavergne, M.; Revillon, A. Makromol. Chem. 1978, 179, 1151-1157.
10. Kresta, J.; Tkác, A.; Prikryl, R.; Malik, L. J. Elastoplast. 1973, 5, 20-35.
11. Kresta, J.; Tkác, A.; Prikryl, R.; Malik, L. Makromol. Chem. 1975, 176, 157-175.
12. Viersen, F. J.; Challa, G.; Reedijk, J. Polymer 1990, 31, 1368-1373.
13. Baesjou, P. J.; Driessen, W. L.; Challa, G.; Reedijk, J. J. Mol. Catal. A 1996, 110, 195-210.
14. Spartan SGI, Ver. 3.1.2 GL, Wavefunction Inc., 1994.
15. Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571-572.
16. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986; p 548.
17. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
18. Antona, P. D.; Longchambon, F.; Vandenborre, M. T.; Becker, P. Acta Crystallogr. 1973, B29, 1372.
19. Li, Y.; Abramovitch, R. A.; Houk, K. N. J. Org. Chem. 1989, 54, 2911-2914.
20. Bernardi, F.; Bottoni, A.; Casadio, R.; Fariselli, P.; Rigo, A. Inorg. Chem. 1996, 35, 5207-5212.
21. Challa, G.; Chen, W.; Reedijk, J. Makromol. Chem., Macromol. Symp. 1992, 59, 59-74.
22. Chen, W. Ph.D. Thesis, Groningen University, 1991.
23. Viersen, F. J.; Challa, G.; Reedijk, J. Recl. Trav. Chim. Pays-Bas 1990, 109, 97-101.
24. Heitz, W. Pure Appl. Chem. 1995, 67, 1951-1964.
25. Cosgrove, S. L.; Waters, W. A. J. Chem. Soc. 1951, 388.
26. Walling, C.; Hodgon, R. B., Jr. J. Am. Chem. Soc. 1958, 80, 228-233.
27. Hay, A. S. J. Polym. Sci. 1962, 58, 581-591.
28. Finkbeiner, H. L.; Hay, A. S.; White, D. M. In Polymerization Processes; Schildknecht, C. E., Ed.; Wiley: New York, 1977; Vol. XXIV, pp 537-581.
29. Benzekri, A.; Dubourdeaux, P.; Latour, J.-M.; Laugier, J.; Rey, P. Inorg. Chem. 1988, 27, 3710-3716.
30. Bolon, D. A. J. Am. Chem. Soc. 1966, 88, 3148.
31. Finkbeiner, H. L.; Endres, G. F.; Blanchard, H. S.; Eustance, J. W. Am. Chem. Soc., Div. Polym. Chem., Prepr. 1961, 2, 340-347.
32. Hay, A. S. Adv. Polym. Sci. 1967, 4, 496-527.
33. Mijs, W. J.; van Lohuizen, O. E.; Bussink, J.; Vollbracht, L. Tetrahedron 1967, 23, 2253-2264.
34. Bolon, D. A. J. Org. Chem. 1967, 32, 1584-1590.
35. Cooper, G. D.; Bennet, J. G. J. Org. Chem. 1972, 37, 441-447.
36. White, D. M. Am. Chem. Soc., Div. Polym. Chem., Prepr. 1968, 9, 663-667.