Atom-transfer reactions catalyzed by methyltrioxorhenium(VII) - Mechanisms and applications

Chemical Communications

Volumn , Issue 6, 1999, Pages 479-488

  Espenson, James H ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; HYDROGEN PEROXIDE; OXIDIZING AGENT; RHENIUM COMPLEX;

ATOM; CATALYSIS; CHEMICAL REACTION; MOLECULE; OXIDATION; REVIEW;

EID: 0033590759     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809222b     Document Type: Review

References (65)

1. C. C. Romão, F. E. Kühn and W. A. Herrmann, Chem. Rev., 1997, 97, 3197.
2. W. A. Herrmann, P. Kiprof, K. Rydpal, J. Tremmel, R. Blom, R. Alberto, J. Behm, R. W. Albach, H. Bock, B. Solouki, J. Mink, D. Lichtenberger and N. E. Gruhn, J. Am. Chem. Soc., 1991, 113, 6527.
3. W. A. Herrmann, J. G. Kuchler, G. Weichselbaumer, E. Herdtweck and P. Kiprof, J. Organomet. Chem., 1989, 372, 351.
4. J. Takacs, M. R. Cook, P. Kiprof, J. G. Kuchler and W. A. Herrmann, Organometallics, 1991, 10, 316.
5. W. A. Herrmann, J. G. Kuchler, P. Kiprof and J. Riede, J. Organomet. Chem., 1990, 395, 55.
6. W.-D. Wang and J. H. Espenson, J. Am. Chem. Soc., 1998, 120, 11335.
7. R. S. Tobias, Organomet. Chem. Rev., 1966, 1, 93-129.
8. G. Strukul, R. Ros and R. A. Michelin, Inorg. Chem., 1982, 21, 495.
9. W. A. Herrmann, R. W. Fischer, W. Scherer and M. U. Rauch, Angew. Chem., Int. Ed. Engl., 1993, 32, 1157.
10. M. Abu-Omar, P. J. Hansen and J. H. Espenson, J. Am. Chem. Soc., 1996, 118, 4966.
11. Dr P. D. Metelski is acknowledged for preparing this experiment and display.
12. P. J. Hansen and J. H. Espenson, Inorg. Chem., 1995, 34, 5839.
13. W.-D. Wang and J. H. Espenson, Inorg. Chem., 1997, 36, 5069.
14. O. Pestovsky, R. van Eldik, P. Huston and J. H. Espenson, J. Chem. Soc., Dalton Trans., 1995, 133.
15. H. Taube, Rec. Chem. Prog., 1956, 17, 277.
16. K. A. Brittingham and J. H. Espenson, Inorg. Chem., in press.
17. G. Laurenczy, F. Lukács, R. Roulet, W. A. Herrmann and R. W. Fischer, Organometallics, 1996, 15, 848.
18. J. H. Espenson, H. Tan, S. Mollah, R. S. Houk and R. D. Eager, Inorg. Chem., 1998, 37, 4621.
19. R. K. Murmann, J. Phys. Chem., 1967, 71, 974.
20. I. Hatzopulos, H.-D. Brauer, M. R. Geisberger and W. A. Herrmann, J. Organomet. Chem., 1996, 520, 201.
21. J. H. Espenson, Chemical Kinetics and Reaction Mechanisms, McGraw-Hill Inc., New York, 2nd edn. 1995.
22. It is this author's opinion that certain disagreements about steady-state kinetics trace to the failure to make a clear distinction between ss and improved-ss treatments: see R. Breslow, J. Chem. Educ., 1990, 67, 228; D. B. Northrop, J. Chem. Educ., 1993, 70, 999; R. Breslow, J. Chem. Educ., 1993, 70, 999.
23. It is this author's opinion that certain disagreements about steady-state kinetics trace to the failure to make a clear distinction between ss and improved-ss treatments: see R. Breslow, J. Chem. Educ., 1990, 67, 228; D. B. Northrop, J. Chem. Educ., 1993, 70, 999; R. Breslow, J. Chem. Educ., 1993, 70, 999.
24. It is this author's opinion that certain disagreements about steady-state kinetics trace to the failure to make a clear distinction between ss and improved-ss treatments: see R. Breslow, J. Chem. Educ., 1990, 67, 228; D. B. Northrop, J. Chem. Educ., 1993, 70, 999; R. Breslow, J. Chem. Educ., 1993, 70, 999.
25. K. A. Vassell and J. H. Espenson, Inorg. Chem., 1994, 33, 5491.
26. A. Al-Ajlouni and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 9243.
27. K. P. Gable, Adv. Organomet. Chem., 1997, 41, 127.
28. D. W. Lahti and J. H. Espenson, unpublished results.
29. G. Strukul, Catalytic Oxidations with Hydrogen Peroxide as Oxidant, Kluwer Academic Publishers, Dordrecht, 1992.
30. (a) H. A. Riley and J. H. Espenson, Inorg. Chem., in press;
31. (b) W. Adam, A. Corna, A. Martinez, C. M. Mitchell, T. I. Ready, M. Renz and A. K. Smerz, J. Mol. Catal. A, 1997, 117, 357.
32. P. C. Buxton, J. N. Ennis, B. A. Marples, V. Waddington and T. R. Boehlow, J. Chem. Soc., Perkin Trans. 2, 1998, 265.
33. A. L. Baumstark, E. Michelena-Baez, A. M. Navarro and H. D. Banks, Heterocycl. Commun., 1997, 3, 393.
34. A. L. Baumstark and L. Vasquez, J. Org. Chem., 1988, 53, 3437.
35. W. A. Schenk, J. Frixch, W. Adam and F. Prechtl, Angew. Chem., Int. Ed. Engl., 1994, 106, 1699.
36. J. Rudolph, K. L. Reddy, J. P. Chiang and K. B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189.
37. C. Coperet, H. Adolfsson and K. B. Sharpless, Chem. Commun., 1997, 1565.
38. M. D. Eager and J. H. Espenson, unpublished information.
39. H. Tan and J. H. Espenson, submitted for publication.
40. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Plenum Press, Part A, 3rd edn., New York, 1990, p. 163.
41. H. Tan and J. H. Espenson, in press.
42. S. Stanković and J. H. Espenson, J. Org. Chem., 1998, 63, 4129.
43. S. Stanković and J. H. Espenson, Chem. Commun., 1998, 1579.
44. R. Fernandez, C. Gasch, J. Lassaletta, J. Llera and J. Vazquez, Tetrahedron Lett., 1993, 34, 141.
45. J. H. Espenson, O. Pestovsky, P. Huston and S. Staudt, J. Am. Chem. Soc., 1994, 116, 2869.
46. A. Mohammed and H. A. Liebhafsky, J. Am. Chem. Soc., 1934, 56, 1680.
47. R. Stewart, in Oxidation Mechanisms: Applications to Organic Chemistry, W. A. Benjamin Inc., New York, 1964.
48. Z. Zhu and J. H. Espenson, J. Org. Chem., 1996, 61, 324.
49. J. Jacob, J. H. Espenson, J. H. Jensen and M. S. Gordon, Organometallics, 1998, 17, 1835.
50. Z. Zhu and J. H. Espenson, Synthesis 1998, 417.
51. Z. Zhu and J. H. Espenson, J. Mol. Catal., 1995, 103, 87.
52. Z. Zhu, A. Al-Ajlouni and J. H. Espenson, Inorg. Chem., 1996, 35, 1408.
53. W. A. Herrmann, P. W. Roesky, M. Wang and W. Scherer, Organometallics, 1994, 13, 4531.
54. M. M. Abu-Omar, E. H. Appleman and J. H. Espenson, Inorg. Chem., 1996, 35, 7751.
55. Z. Zhu, J. H. Espenson, Organometallics, 1997, 16, 3658.
56. Z. Zhu and J. H. Espenson, J. Org. Chem., 1995, 60, 7090.
57. Z. Zhu and J. H. Espenson, J. Am. Chem. Soc., 1996, 118, 9901.
58. I. A. Begnan, J. Behm, M. R. Cook and W. A. Herrmann, Inorg. Chem., 1991, 30, 2165.
59. W. A. Herrmann, J. G. Kuchler, J. K. Felixberger, E. Herdtweck and W. Wagner, Angew. Chem., Int. Ed. Engl., 1988, 27, 394.
60. M. M. Abu-Omar and J. H. Espenson, J. Am. Chem. Soc., 1995, 117, 272.
61. M. M. Abu-Omar and J. H. Espenson, Organometallics, 1996, 15, 3543.
62. K. N. Brown and J. H. Espenson, Inorg. Chem., 1996, 35, 7211.
63. Z. Zhu and J. H. Espenson, J. Org. Chem., 1995, 60, 1326.
64. A. Al-Ajlouni and J. H. Espenson, J. Org. Chem., 1996, 61, 3969.
65. J. Jacob, J. H. Espenson, J. H. Jensen and M. S. Gordon, Organometallics, 1998, 37, 1835.