Oxygenation of alkane C-H bonds with methyl(trifluoromethyl)dioxirane: Effect of the substituents and the solvent on the reaction rate

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 7919-7924

  González Núñez, María E ^a   Royo, Jorge ^a   Mello, Rossella ^a   Báguena, Minerva ^a   Ferrer, Jaime Martínez ^a   De Arellano, Carmen Ramírez ^a   Asensio, Gregorio ^a   Prakash, G K Surya ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; LINEAR SYSTEMS; OXYGEN; REACTION KINETICS;

DEACTIVATION; ELECTRON DEFICIENCY; OXYGENATION; TRANSITION STATE;

CHEMICAL BONDS;

ADAMANTANE DERIVATIVE; CARBON; ETHYLENE OXIDE DERIVATIVE; METHYL(TRIFLUOROMETHYL)DIOXIRANE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; DIASTEREOISOMER; ELECTRON; OXYGENATION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 25444499499     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0509511     Document Type: Article

References (66)

1. (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205-211.
2. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187-1201.
3. (c) Curci, R. Adv. Oxygenated Processes (1990) 2, 1-59.
4. (d) Adam, W.; Hadjiaropoglou, L.; Curci, R.; Mello, R. Organic Peroxides; Wiley: Chichester, 1992; pp 195-219.
5. (e) Clennan, E. L. Trends Org. Chem. 1995, 5, 231-252.
6. (f) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581-599.
7. (g) Adam, W., Ed. Peroxide Chemistry; Wiley-VCH: Weinheim, 2000.
8. (h) Adam, W.; Saha-Moller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499-3548.
9. (a) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749-6757.
10. (b) Asensio, G.; González-Núñez, M. E.; Mello, R.; Boix-Bernardini, C.; Adam, W. J. Am. Chem. Soc. 1993, 115, 7250-7253.
11. (c) Kuck, D.; Schuster, A.; Fusco, C.; Fiorentino, M.; Curci, R. J. Am. Chem. Soc. 1994, 116, 2375-2381.
12. (d) Asensio, G.; Mello, R.; González-Núñez, M. E.; Castellano, G.; Corral, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 217-218.
13. (e) Asensio, G.; Castellano, G.; Mello, R.; González- Núñez, M. E. J. Org. Chem. 1996, 61, 5564-5566.
14. (f) Curci, R.; Detomaso, A.; Lattanzio, M. E.; Carpenter, G. B. J. Am. Chem. Soc. 1996, 118, 11089-11092.
15. (g) Fusco, C.; Fiorentino, M.; Dinoi, A.; Curci, R. J. Org. Chem. 1996, 61, 8681-8684.
16. (h) Yang, D.; Wong, M. K.; Wang, X. C.; Tang, Y. C. J. Am. Chem. Soc. 1998, 120, 6611-6612.
17. (i) D'Accolti, L.; Dinoi, A.; Fusco, C.; Russo, A.; Curci, R. J. Org. Chem. 2003, 68, 7806-7810.
18. (j) Won, M.-K.; Chung, N.-W.; He, L.; Wang, X.-C.; Yan, Z.; Tang, Y.-C.; Yang, D. J. Org. Chem. 2003, 68, 6321-6328.
19. (k) Wong, M. K.; Chung, N. W.; He, L.; Yang, D. J. Am. Chem. Soc. 2003, 125, 158-162.
20. (l) D'Accolti, L.; Fusco, C.; Annese, C.; Rella, M. R.; Turteltaub, J. S.; Williard, P. G.; Curci, R. J. Org. Chem. 2004, 69, 8510-8513.
21. (a) Adam, W.; Asensio, G.; Curci, R.; Gonzalez-Nuñez, M. E.; Mello, R. J. Org. Chem. 1992, 57, 953-955.
22. (b) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
23. (a) Bravo, A.; Fontana, G.; Fronza, G.; Minisci, F. J. Chem. Soc., Chem. Commun. 1995, 1573-1574.
24. (b) Bravo, A.; Fontana, G.; Minisci, F. Tetrahedron Lett. 1995, 38, 6945-6948.
25. (c) Minisci, F.; Zhao, L.; Fontana, F.; Bravo, A. Tetrahedron Lett. 1995, 36, 1697-1700.
26. (d) Vanni, R.; Garden, S. J.; Banks, J.; Ingold, K. U. Tetrahedron Lett. 1995, 36, 7999-8002.
27. (e) Bravo, A.; Fontana, F.; Fronza, G.; Minisci, F.; Zhao, L. J. Org. Chem. 1998, 63, 254-263.
28. (f) Simakov, P. A.; Choi, S. Y.; Newcomb, M. Tetrahedron Lett. 1998, 39, 8187-8190.
29. (a) Glukhovtsev, M. N.; Canepa, C.; Bach, R. D. J. Am. Chem. Soc. 1998, 120, 10528-10533.
30. (b) Du, X.; Houk, K. N. J. Org. Chem. 1998, 63, 6480-6483.
31. (c) Shustov, G. V.; Rauk, A. J. Org. Chem. 1998, 63, 5413-5422.
32. (c) Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M.; Rastelli, A. J. Org. Chem. 2003, 68, 811-823.
33. Asensio, G.; Mello, R.; González-Núñez, M. E.; Boix, C.; Royo, J. Tetrahedron Lett. 1997, 38, 2373-2376.
34. Fokin, A. A.; Tkachenko, B. A.; Korschunov, O. I.; Gunchenko, P. A.; Schreiner, P. R. J. Am. Chem. Soc. 2001, 123, 11248-11252.
35. (a) González-Núñez, M. E.; Royo, J.; Castellano, G.; Andreu, C.; Boix, C.; Mello, R.; Asensio, G. Org. Lett. 2000, 2, 831-834.
36. (b) González-Núñez, M. E.; Castellano, G.; Andreu, C.; Royo, J.; Báguena, M.; Mello, R.; Asensio, G. J. Am. Chem. Soc. 2001, 123, 7487-7491.
37. Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119-251.
38. Murray, R. W.; Gu, H. J. Org. Chem. 1995, 60, 5673-5677.
39. Adam, W.; Curci, R.; González-Núñez, M. E.; Mello, R. J. Am. Chem. Soc. 1991, 113, 7654-7658.
40. (a) Grob, C. A.; Schlageter, M. G. Helv. Chim. Acta 1976, 59, 264-276.
41. (b) Grob, C. A.; Schaub, B.; Schalgeter, M. G. Helv. Chim. Acta 1980, 63, 57-62.
42. (a) Grob, C. A.; Schlageter, M. G. Helv. Chim. Acta 1976, 59, 264-276.
43. (b) Grob, C. A.; Schaub, B.; Schlageter, M. G. Helv. Chim. Acta 1980, 63, 57-62.
44. (c) Grob, C. A. Acc. Chem. Res. 1983, 16, 426-431.
45. Schneider, H.-J.; Müller, W. J. Org. Chem. 1985, 50, 4609-4615.
46. (a) Lovins, R. E.; Andrews, L. J.; Reefer, R. M. J. Org. Chem. 1965, 30, 1577-1580.
47. (b) Fischer, T. H.; Meierhoefer, A. W. J. Org. Chem. 1978, 43, 220-224.
48. (c) Davies, W. H., Jr.; Pryor, W. A. J. Am. Chem. Soc. 1977, 99, 6365-6372.
49. (d) Tanner, D. D.; Samal, P. W.; Ruo, T. C.-S.; Henriquez, R. J. Am. Chem. Soc. 1979, 101, 1168-1175.
50. (e) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987.
51. Fukunichi, K.; Kohno, A.; Kojo, S. J. Org. Chem. 1988, 53, 4369-4374.
52. (a) Reichardt, C. Pure Appl. Chem. 1982, 54, 1867-1884.
53. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, Germany, 1988.
54. (a) Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
55. (b) Lucarini, M.; Pedulli, G. F.; Valgimigli, L. J. Org. Chem. 1998, 63, 4497-4499.
56. (c) Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
57. Dimroth, K.; Reichardt, C.; Siepmann, T.; Bohlmann, F. Liebigs Ann. Chem. 1963, 661, 1-37.
58. (a) Partington, J. R. An Advanced Treatise on Physical Chemistry; Longmans, Green and Co.: London, 1951; Vol. 2, p 2ff
59. and An Advanced Treatise on Physical Chemistry; Vol. 5, p 390ff.
60. (b) Knauer, B. R.; Napier, J. J. J. Am. Chem. Soc. 1976, 98, 4395-4400.
61. (c) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. H. J. Am. Chem. Soc. 1992, 114, 4983-4992.
62. Murray, R. W.; Gu, D. J. Chem. Soc., Perkin Trans. 2 1994, 451-453.
63. Kamlet, M. J.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877-2887.
64. (a) Adcock, W.; Trout, N. A. Magn. Res. Chem. 1998, 36, 181-195.
65. (b) Adcock, W.; Trout, N. A. J. Org. Chem. 1991, 56, 3229-3238.
66. (c) Cheung, C. K.; Tseng, L. T.; Lin, M.-H.; Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1986, 108, 1598-1605.