Theoretical and experimental studies on mechanism and rate constant for the Baeyer-Villiger oxidation of cyclohexanone by H2O2 in phenol

Journal of Molecular Structure: THEOCHEM

Volumn 901, Issue 1-3, 2009, Pages 117-127

  Long, Qingping ^a   Ji, Hongbing ^a   Lu, Shushen ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Baeyer Villiger oxidation; Concerted mechanism; Density function theory; Rate constant

Indexed keywords

EID: 62949245623     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.01.012     Document Type: Article

References (41)

1. Baeyer A., and Villiger V. Chem. Ber. 32 (1899) 3625
2. Sanchidrián C.J., Hidalgo J.M., Llamas R., and Ruiz J.R. Appl. Catal. A-Gen. 312 (2006) 86
3. Renz M., and Meunier B. Eur. J. Org. Chem. (1999) 737
4. Carlqvist P., Eklund R., Hult K., and Brinck T. J. Mol. Model. 9 (2003) 164
5. Grein F., Chen A.C., Edwards D., and Crudden C.M. J. Org. Chem. 71 (2006) 861
6. Singleton D.A., and Szymanski M.J. J. Am. Chem. Soc. 121 (1999) 9455
7. Kjonaas R.A., and Clemons A.E. Chem. Educ. 85 (2008) 827
8. Lambert A., Elings J.A., Macquarrie D.J., Carr G., and Clark J.H. Synlett (2000) 1052
9. Kotsuki H., Arimura K., Araki T., and Shinohara T. Synlett (1999) 462
10. Watanabe A., Uchida T., Ito K., and Katsuki T. Tetrahedron Lett. 43 (2002) 4481
11. Renz M., Blasco T., Corma A., Fornés V., Jensen R., and Nemeth L. Chem. Eur. J. 8 (2002) 4708
12. ten Brink G.J., Vis J.M., Arends I.W.C.E., and Sheldon R.A. J. Org. Chem. 66 (2001) 2429
13. Phillips A.M.F., and Romão C. Eur. J. Org. Chem. 1999 (1999) 1767
14. Corma A., Navarro M.T., Nemeth L., and Renz M. Chem. Commun. (2001) 2190
15. Cárdenas R., Cetina R., Lagúnez-Otero J., and Reyes L. J. Phys. Chem. A 101 (1997) 192
16. Carlqvist P., Eklund R., and Brinck T. J. Org. Chem. 66 (2001) 1193
17. Sever R.R., and Root T.W. J. Phys. Chem. B107 (2003) 10848
18. Sever R.R., and Root T.W. J. Phys. Chem. B 107 (2003) 10521
19. Yamabe S., and Yamazaki S. J. Org. Chem. 72 (2007) 3031
20. Alvarez-Idaboy J.R., Reyes L., and Cruz J. Org. Lett. 8 (2006) 1763
21. Alvarez-Idaboy J.R., Reyes L., and Mora-Diez N. Org. Biomol. Chem. 5 (2007) 3682
22. Neimann K., and Neumann R. Org. Lett. 2 (2000) 2861
23. Steffen R.A., Teixeira S., Sepulveda J., Rinaldi R., and Schuchardt U. J. Mol. Catal. A: Chem. 287 (2008) 41
24. Li J.X., Le Y.Y., Dai W.L., Li H.X., and Fan K.N. Catal. Commun. 9 (2008) 1334
25. Boronat M., Corma A., Renz M., Sastre G., and Viruela P.M. Chem. Eur. J. 11 (2005) 6905
26. M.J. Frisch, G.W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision D.01; Gaussian Inc., Wallingford, CT, 2003.
27. B. James, F.E. Frisch, Exploring Chemistry with Electronic Structure Methods, second ed., Gaussian, Inc., USA, 1996.
28. Gonzalez C., and Schlegel H.B. J. Phys. Chem. 94 (1990) 5523
29. Curtiss L.A., Redfern P.C., Smith B.J., and Radom L. J. Chem. Phys. 104 (1996) 5148
30. Cossi M., Barone V., Cammi R., and Tomasi J. Chem. Phys. Lett. 255 (1996) 327
31. Barone V., Cossi M., and Tomasi J. J. Chem. Phys. 107 (1997) 3210
32. Eyring H. J. Chem. Phys. 3 (1935) 107
33. Bravo-Pérez G., Alvarez-Idaboy J.R., Cruz-Torres A., and Ruíz M.E. J. Phys. Chem. A 106 (2002) 4645
34. Pechukas P. In: Miller W.H. (Ed). Dinamics of Molecular Collisions, Part B (1976), Plenum Press, New York
35. Pollak E., and Pechukas P. J. Am. Chem. Soc. 100 (1978) 2984
36. Stoute V.A., Winnik M.A., and Csizmadia I.G. J. Am. Chem. Soc. 96 (1974) 6388
37. Crudden C.M., Chen A.C., and Calhound L.A. Angew. Chem. Int. Ed. 39 (2000) 2851
38. Smith M.B., and March J. March's Advanced Organic Chemistry: Reactions, Mechanisms and Structures. sixth ed. (2007), Wiley, Hoboken, New Jersey
39. Long Q.P., Ji H.B., and Lv S.S. Int. J. Quantum Chem. 109 (2009) 448
40. Benson S.W. The Foundations of Chemical Kinetics (1982), Krieger, Florida
41. Xu Y. The Kinetics of Organic Reaction (2004), Chemical Industry Press, Beijing