Oxidation of substituted toluenes with molecular oxygen in the presence of N,N′,N″-Trihydroxyisocyanuric acid as a key catalyst

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6587-6590

  Hirai, Naruhisa ^a   Sawatari, Naoko ^b   Nakamura, Norihiro ^b   Sakaguchi, Satoshi ^b   Ishii, Yasutaka ^b  

^a DAICEL CORPORATION   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYSTS; ELECTRONS; OXIDATION; OXYGEN;

QUANTITATIVE YIELDS;

TOLUENE;

BENZOIC ACID; CYANURIC ACID; N,N',N'' TRIHYDROXYISOCYANURIC ACID; OXYGEN; PHTHALIC ACID; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG; XYLENE;

ARTICLE; CATALYST; ELECTRON TRANSPORT; OXIDATION; QUANTUM YIELD; REACTION OPTIMIZATION; SUBSTITUTION REACTION;

EID: 0043011084     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034313z     Document Type: Article

References (16)

1. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992; p 225.
2. (b) Park, C. J.; Sheehan, R. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwite, J. I., Howe-Grant, M., Eds.; John Wiley and Sons: New York, 1996; Vol. 18, p 991.
3. (c) Sheehan, J. R. In Ullmann's Encyclopedia Industrial Organic Chemicals; Ullmann, F., Ed.; Wiley-VCH: Weinheim, Germany, 1999; Vol. 8, p 4575.
4. (d) Partenheimer, W. Catal. Today 1995, 23, 69.
5. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth, Catal. 2001, 343, 393.
6. Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
7. Amorati, R.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F.; Minisci, F.; Recupero, F.; Fontana, F.; Astolfi, P.; Greci, L. J. Org. Chem. 2003, 68, 1747.
8. The O-H bond dissociation energy of THICA and NHPI was calculated using the PMP2/6-31++G**//HF/6-31G** level of theory.
9. (a) Robertson, D. W.; Krushinski, J. H.; Beedle, E. E. J. Med. Chem. 1987, 30, 552.
10. (b) Koyama, M.; Ohtani, N.; Fumio, K. J. Med. Chem. 1985, 28, 717.
11. Levine, M.; Sedlecky, R. J. Org. Chem. 1959, 24, 115.
12. Sasson, Y.; Zappi, G. D.; Neuman, R. J. Org. Chem. 1986, 51, 2880.
13. Das, B. K.; Clark, J. H. Chem. Commun. 2000, 605.
14. Milind, D.; Sudalai, A. Tetrahedron 1999, 55, 5903.
15. (a) Butula, I.; Takac, M. Croat. Chem. Acta 2000, 2, 569.
16. (b) Staab, H. A.; Benz, W. Angew. Chem. 1961, 73, 657.