Remarkable effect of water on functionalization of the phenyl ring in methyl-substituted benzene derivatives with F-TEDA-BF4

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3880-3888

  Kralj, Petra ^a   Zupan, Marko ^a,b   Stavber, Stojan ^a  

^a JO EF STEFAN INSTITUTE   (Slovenia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; DERIVATIVES; KETONES; REACTION KINETICS; SOLVENTS; WATER;

METHYL-SUBSTITUTED BENZENE DERIVATIVES; PHENYL RING TRANSFORMATION; PROTIC SOLVENTS; TRIFLUOROACETIC ACID;

BENZENE;

1 CHLOROMETHYL 4 FLUORO 1,4 DIAZONIABICYCLO[2.2.]OCTANE BIS(TETRAFLUOROBORATE); 1,2,3,4,5,6 HEXAMETHYLBICYCLO[2.2.0]HEXA 2,5 DIENE; 1,3,5 TRIMETHYLBENZENE; 2,3,4,5 TETRAMETHYLPHENOL; 2,3,4,5,6,6 HEXAMETHYLCYCLOHEXA 2,4 DIENONE; 4 FLUORO 2,3,4,5 TETRAMETHYLCYCLOHEXA 2,5 DIENONE; 5 FLUORO 2,3,5,6,6 PENTAMETHYL 4 METHYLENECYCLOHEX 2 EN 1 ONE; 5 HYDROXY 2,3,5,6,6 PENTAMETHYL 4 METHYLENECYCLOHEX 2 EN 1 ONE; ACETONITRILE; ALKANONE; BENZENE DERIVATIVE; CRESOL; DURENE; ESTER; HEXAMETHYLBENZENE; METHYL GROUP; OXIDE; PHENYL GROUP; PREHNITENE; REAGENT; SOLVENT; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 33646508763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060213s     Document Type: Article

References (75)

1. (a) Li, C-J.; Chan, T.-H. Organic Reactions in Aqueous Media; J. Wiley&Sons: New York, 1997.
2. (b) Adams, D. J.; Dyson, P. J.; Tavener, S. J. Chemistry In Alternative Reaction Media; J. Wiley&Sons: Chichester, UK, 2004.
3. (c) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741-760.
4. Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772.
5. (e) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095-4101.
6. (f) Otto, S.; Engberts, B. F. N. Org. Biomol. Chem. 2003, 1, 2809-2820.
7. (a) Li, C. J. Tetrahedron 1996, 52, 5643-5668.
8. (b) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149-11176.
9. (c) Li, C. J. Green Chem. 2002, 4(1), 1-4.
10. (d) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209-217.
11. (e) Okuhara, T. Chem. Rev. 2002, 102, 3641-3666.
12. (f) Miyabe, H.; Naito, T. Org. Biomol. Chem. 2004, 2, 1267-1270.
13. (g) Li, C. J. Chem. Rev. 2005, 105, 3095-3165.
14. Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 5, 674-686.
15. (a) Breslow, R. Acc. Chem. Res. 1991, 24, 159-164.
16. (b) Breslow, R.; Groves, K.; Mayer, M. U. J. Am. Chem. Soc. 2002, 124, 3622-3635.
17. (c) Breslow, R. Acc. Chem. Res. 2004, 37, 471-478.
18. (a) Hofmann, M.; Hampel, N.; Kanzian, T.; Mayr, H. Angew. Chem., Int. Ed. 2004, 43, 5402-5405.
19. (b) Minegishi, S.; Kobayashi, S.; Mayr, H. J. Am. Chem. Soc. 2004, 126, 5174-5181.
20. For further reading on the role of acceptor and donor on the reactivity of organic molecules see: (c) Mayr, H. Angew. Chem. 1990, 102, 1415-1428.
21. (d) Mayr, H.; Patz, M. Angew. Chem. 1994, 106, 990-1010.
22. (e) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
23. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279.
24. (a) Bose, A. K.; Manhas, M. S.; Ganguly, S. N.; Pednekar, S.; Mandadi, A. Tetrahedron Lett. 2005, 46, 3011-3013.
25. (b) Bose, A. K.; Manhas, M. S.; Pednekar, S.; Ganguly, S. N.; Dang, H.; He, W.; Mandadi, A. Tetrahedron Lett. 2005, 46, 1901-1903.
26. Stavber, G.; Zupan, M.; Jereb, M.; Stavber, S. Org. Lett. 2004, 6, 4973-4976 and references therein.
27. Jereb, M.; Zupan, M.; Stavber, S. Chem. Commun. 2004, 2614-2615.
28. Pavlinac, J.; Zupan, M.; Stavber, S. J. Org. Chem. 2006, 71, 1027-1032.
29. (a) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360.
30. (b) Kochi, J. K. Angew. Chem. 1988, 100, 1331-1372.
31. (c) Kochi, J. K. Acta Chem. Scand. 1990, 44, 409-432.
32. (d) Kochi, J. K. Acc. Chem. Res. 1992, 25, 39-47.
33. (e) Kochi, J. K. Electron Transfer in the Thermal and Photochemical Activation of Electron Donor-Acceptor Complexes in Organic and Organometallic Reactions. Adv. Phys. Org. Chem. 1994, 29, 185-272.
34. (f) Hubig, S. M.; Kochi, J. K. J. Org. Chem. 2000, 65, 6807-6818.
35. (g) Rosokha, S. V.; Kochi, J. K. J. Org. Chem. 2002, 67, 1727-1737.
36. Taylor, R. Electrophilic Aromatic Substitution; J. Wiley&Sons: Chichester, UK, 1990.
37. (a) Galli, C. J. Org. Chem. 1991, 56, 3238-3245.
38. (b) Fabbrini, M.; Galli, C.; Gentili, P.; Macchitella, D.; Petride, H. J. Chem. Soc., Perkin Trans. 2 2001, 1516-1521 and references therein.
39. Bockman, T. M.; Kochi, J. K. J. Phys. Org. Chem. 1994, 7, 325-351 and references therein.
40. Baciocchi, E.; Galli, C. J. Phys. Org. Chem. 1995, 8, 563-565.
41. Zupan, M. Chimia 1976, 305-306.
42. Zupan, M.; Stavber, S. The role of reagent structure in the mild introduction of a fluorine atom into organic molecules: Xenon difluoride, caesium fluoroxysulphate and F-TEDA case. In Trends Org. Chem. 1995, 5, 11-36 and references therein.
43. Kol, M.; Rozen, S. J. Org. Chem. 1993, 58, 1593-1595.
44. Bockman, T. M.; Lee, K. Y.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1992, 1581-1594.
45. Stavber, S.; Kralj, P.; Zupan, M. Synlett 2001, 7, 1152-1154.
46. Stavber, S.; Zupan, M. J. Org. Chem. 1983, 48, 2223-2226.
47. Stavber, S.; Zupan, M. J. Org. Chem. 1991, 56, 7347-7350.
48. Laali, K. K.; Borodkin, G. I. J. Chem. Soc., Perkin Trans. 2 2002, 953-957.
49. Lee, K. Y.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1992, 1011-1017.
50. (a) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
51. (b) Banks, R. E. J. Fluorine Chem. 1998, 87, 1-17.
52. (c) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431-12477.
53. (d) Singh, R. P.; Shreeve, J. M. Acc. Chem. Res. 2004, 37, 31-44.
54. (e) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew. Chem., Int. Ed. 2005, 44, 192-212.
55. (f) Stavber, S.; Zupan, M. Acta Chim. Slov. 2005, 52, 13-26.
56. (g) Stavber, S.; Zupan, M. N-Fluoro-1,4-Diazoniabicyclo-[2.2.2]octane Dication Salts; Efficient Fluorinating Agents and Functionalization Mediators for Organic Compounds. In Advances in Organic Synthesis; Rahman, A., Laali, K., Eds.; Bentham Science Publisher Ltd.: San Francisco, CA, 2006; Vol. 2, pp 213-267.
57. Schmittel, M.; Burghart, A. Angew. Chem. 1997, 109, 2658-2699.
58. Balzani, V., Ed. Electron Transfer in Chemistry; Willey-VCH: Weinheim, Germany, 2001: Vol. 2.
59. Eberson, L.; Hartshorn, M. P.; Persson, O.; Radner, F. Chem. Commun. 1996, 2105-2112.
60. Bégué, J. P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 1, 18-29.
61. Hart, H.; Collins, P. M.; Waring, A. J. J. Am. Chem. Soc. 1966, 88, 1005-1013.
62. Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999-1005.
63. (a) Stavber, S.; Sotler-Peèan, T.; Zupan, M. J. Chem. Soc., Perkin Trans. 2 2000, 1141-1145.
64. (b) Stavber, S.; Sotler-Peèan, T.; Zupan, M. Tetrahedron 2000, 56, 1929-1936.
65. (a) Stavber, S.; Jereb, M.; Zupan, M. Arkivoc 2001, 98-107.
66. (b) Stavber, S.; Jereb, M.; Zupan, M. J. Phys. Org. Chem. 2002, 15, 56-61.
67. Zupan, M.; Papež, M.; Stavber, S. J. Fluorine Chem. 1996, 78, 137-140.
68. (a) Stavber, S.; Jereb, M.; Zupan, M. Synlett 1999, 9, 1375-1378.
69. (b) Jereb, M.; Zupan, M.; Stavber, S. Arkivoc 2003, 187-197.
70. (a) Stavber, S.; Sotler-Peèan, T.; Papež, M.; Zupan, M. Chem. Commun. 1996, 2247-2248.
71. (b) Zupan, M.; Skulj, P.; Stavber, S. Tetrahedron 2001, 57, 10027-10031.
72. Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3968-3976.
73. Baciocchi, E.; Mandolini, L. Tetrahedron 1987, 43, 4035-4041.
74. Chiappe, C.; Pieraccini, D. Arkivoc 2002, 249-255.
75. Fabbrini, M.; Galli, C.; Gentili, P.; Macchitella, D.; Petride, H. J. Chem. Soc., Perkin Trans. 2 2001, 1516-1521.