Theoretical study on the regioselectivity of baeyer-villiger reaction of α-Me-, -F-, -CF3-cyclohexanones

Journal of Organic Chemistry

Volumn 78, Issue 1, 2013, Pages 146-153

  Itoh, Yoshimitsu ^a,b   Yamanaka, Masahiro ^c   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY BARRIERS; STABILIZATION;

ACID MOIETY; AXIAL ORIENTATIONS; BAEYER-VILLIGER REACTION; CATION STABILIZATION; CYCLOHEXANONES; DIPOLE INTERACTION; ENERGY PROFILE; KINETIC REACTIVITY; MIGRATORY APTITUDE; POSITIVE CHARGES; STERIC REPULSIONS; STRUCTURAL STABILITIES; THEORETICAL STUDY; TRANSITION STATE;

REGIOSELECTIVITY;

CYCLOHEXANONE DERIVATIVE;

ARTICLE; BAEYER VILLIGER REACTION; CHEMICAL INTERACTION; CHEMICAL MODEL; CONFORMATION; DIPOLE; ELECTRON; ENERGY; ENERGY TRANSFER; KINETICS; MOLECULAR STABILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; THEORETICAL STUDY;

EID: 84962463263     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302151r     Document Type: Article

References (57)

1. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633.
2. Krow, G. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 7, p 671.
3. Krow, G. R. Org. React. 1993, 43, 251-798.
4. Strukul, G. Angew. Chem., Int. Ed. 1998, 37, 1198-1209.
5. Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750.
6. Brink, G.-J.; ten Arends, I. W. C. E.; Sheldon, R. A. Chem. Rev. 2004, 104, 4105-4123.
7. Ireland, R. E.; Maienfisch, P. J. Org. Chem. 1988, 53, 640-651.
8. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127-135.
9. Friess, S. L.; Soloway, A. H. J. Am. Chem. Soc. 1951, 73, 3968-3972.
10. Hawthorne, M. F.; Emmons, W. D. J. Am. Chem. Soc. 1958, 80, 6398-6404.
11. Ogata, Y.; Sawaki, Y. J. Org. Chem. 1969, 34, 3985-3991.
12. Palmer, B. W.; Fry, A. J. Am. Chem. Soc. 1970, 92, 2580-2581.
13. Ogata, Y.; Sawaki, Y. J. Am. Chem. Soc. 1972, 94, 4189-4196.
14. Ogata, Y.; Sawaki, Y. J. Org. Chem. 1972, 37, 2953-2957.
15. Winnik, M. A.; Stoute, V. Can. J. Chem. 1973, 51, 2788-2793.
16. Winnik, M. A.; Stoute, V.; Fitzgerald, P. J. Am. Chem. Soc. 1974, 96, 1977-1979.
17. Singleton, D. A.; Szymanski, M. J. J. Am. Chem. Soc. 1999, 121, 9455-9456.
18. Noyori, R.; Sato, T.; Kobayashi, H. Tetrahedron Lett. 1980, 21, 2569-2572.
19. Noyori, R.; Kobayashi, H.; Sato, T. Tetrahedron Lett. 1980, 21, 2573-2576.
20. Chandrasekhar, S.; Roy, C. D. Tetrahedron Lett. 1987, 28, 6371-6372.
21. Crudden, C. M.; Chen, A. C.; Calhoun, L. A. Angew. Chem., Int. Ed. 2000, 39, 2852-2855.
22. Itoh, Y.; Yamanaka, M.; Mikami, K. Org. Lett. 2003, 5, 4803-4806.
23. Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393.
24. Cardenas, R.; Cetina, R.; Lagünez-Otero, J.; Reyes, L. J. Phys. Chem. A 1997, 101, 192-200.
25. Okuno, Y. Chem.Eur. J. 1997, 3, 212-218.
26. Hannachi, H.; Anoune, N.; Arnaud, C.; Lanteri, P.; Longeray, R.; Chermette, H. J. Mol. Struct. 1998, 434, 183-191.
27. Cadenas, R.; Reyes, L.; Lagünez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225.
28. Lehtinen, C.; Nevalainen, V.; Brunow, G. Tetrahedron 2000, 56, 9375-9382.
29. Carlqvist, P.; Eklund, R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
30. Lehtinen, C.; Nevalainen, V.; Brunow, G. Tetrahedron 2001, 57, 4741-4751.
31. Carlqvist, P.; Eklund, R.; Hult, K.; Brinck, T. J. Mol. Model. 2003, 9, 164-171.
32. Sever, R. R.; Root, T. W. J. Phys. Chem. B 2003, 107, 10848-10862.
33. Snowden, M.; Bermudez, A.; Kelly, D. R.; Radkiewicz-Poutsma, J. L. J. Org. Chem. 2004, 69, 7148-7156.
34. Boronat, M.; Corma, A.; Renz, M.; Sastre, G.; Viruela, P. M. Chem.Eur. J. 2005, 11, 6905-6915.
35. Reyes, L.; Castro, M.; Cruz, J.; Rubio, M. J. Phys. Chem. A 2005, 109, 3383-3390.
36. Grein, F.; Chen, A. C.; Edwards, D.; Crudden, C. M. J. Org. Chem. 2006, 71, 861-872.
37. Alvarez-Idaboy, J. R.; Reyes, L.; Cruz, J. Org. Lett. 2006, 8, 1763-1765.
38. Kovacs, A.; Nemcsok, D. S.; Keglevich, G. Heteroat. Chem. 2007, 18, 759-766.
39. Yamabe, S.; Yamazaki, S. J. Org. Chem. 2007, 72, 3031-3041.
40. Alvarez-Idaboy, J. R.; Reyes, L. J. Org. Chem. 2007, 72, 6580-6583.
41. Alvarez-Idaboy, J. R.; Reyes, L.; Mora-Diez, N. Org. Biomol. Chem. 2007, 5, 3682-3689.
42. Reyes, L.; Alvarez-Idaboy, J. R.; Mora-Diez, N. J. Phys. Org. Chem. 2009, 22, 643-649.
43. Mora-Diez, N.; Keller, S.; Alvarez-Idaboy, J. R. Org. Biomol. Chem. 2009, 7, 3682-3690.
44. Xu, S.; Wang, Z.; Li, Y.; Zhang, X.; Wang, H.; Ding, K. Chem.Eur. J. 2010, 16, 3021-3035.
45. Liu, B.; Meng, X.-G.; Li, W.-Y.; Zhou, L.-C.; Hu, C.-W. J. Phys. Chem. A 2012, 116, 2920-2926.
46. Reyes, L.; Díaz-Sanchez, C.; Iuga, C. J. Phys Chem. A 2012, 116, 7712-7717.
47. Becke, A. D. Phys. Rev. 1988, A38, 3098-3100.
48. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
49. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
50. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-788.
51. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908-6918.
52. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493.
53. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093.
54. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
55. Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
56. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
57. Jensen, F. R.; Bushweller, C. H. Adv. Alicyclic Chem. 1971, 3, 139-195.