Host-guest chemistry in a urea matrix: Catalytic and selective oxidation of triorganosilanes to the corresponding silanols by methyltrioxorhenium and the urea/hydrogen peroxide adduct

Journal of the American Chemical Society

Volumn 121, Issue 10, 1999, Pages 2097-2103

  Adam, Waldemar ^a   Mitchell, Catherine M ^a   Sana Möller, Chantu R ^a   Weichold, Oliver ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN PEROXIDE; SILANE DERIVATIVE; UREA;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DECOMPOSITION; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033577285     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9826542     Document Type: Article

References (78)

1. (a) Mimoun, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 734-750.
2. (b) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
3. (c) Jørgensen, K. A. Chem. Rev. 1989, 89, 431-458.
4. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
5. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
6. (c) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801-2803.
7. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
8. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
9. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
10. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
11. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
12. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
13. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
14. Epoxidation of olefins: (a) Herrmann, W. R.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638-1641. (b) Hermann, W. R.; Fischer, R. W.; Rauch, M. U.; Scherer, W. J. Mol. Catal. 1994, 86, 243-266. (c) Al-Ajlouni, A. M.; Espenson, J. H. J. Am. Chem. Soc. 1995, 117, 9243-9250. (d) Adam, W.; Mitchell, C. M. Angew. Chem., Int Ed. Engl. 1996, 35, 533-535. (e) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969-3976. Sulfoxidation: (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron 1994, 50, 13121-13124. (g) Vassell, K. A.; Espenson, J. H. Inorg. Chem. 1994, 33, 5491-5498. Arene oxidation: (h) Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Möller, C. R.; Fischer, R. W.; Correia, J. D. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2475-2477.
15. Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T. Tetrahedron Lett. 1995, 36, 6415-6418.
16. Lickiss, P. D. Adv. Inorg. Chem. 1995, 42, 147-262.
17. Fessenden, R. J.; Fessenden, J. S. Adv. Organomet. Chem. 1980, 18, 275-299.
18. (a) Steiling, L.; Tacke, R.; Wannagat, U. Liebigs Ann. Chem. 1979, 1554-1559.
19. (b) Tacke, R.; Strecker, M.; Sheldrick, W. S.; Heeg, E.; Berndt, B.; Knapstein, K. M. Z. Naturforsch., Teil B 1979, 34, 1279-1285.
20. (c) Tacke, R.; Strecker, M.; Sheldrick, W. S.; Ernst, L.; Heeg, E.; Berndt, B.; Knapstein, C.-M.; Nieder, R. Chem. Ber. 1980, 113, 1962-1980.
21. (d) Tacke, R.; Pikies, J.; Linoh, H.; Rohr-Aehle, R.; Gönne, S. Liebigs Ann. Chem. 1987, 51-57.
22. (e) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237.
23. (f) Gueyne, J.; Seguin, M.-C. U.S. Patent 4,927,952.
24. Riedel, E. Anorganische Chemie; Walter de Gruyter: Berlin, 1988; p 500.
25. (a) Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1959, 3404-3411.
26. (b) Eaborn, C. Organosilicon Compounds; Butterworth: London, 1960.
27. (c) Harris, G. I. J. Chem. Soc. 1963, 5978-5982.
28. In the oxidation of dimethylethylsilane with dimethyldioxirane, a chemoselectivaty (silanol versus disiloxane) of only ca 23:77 is observed after workup. Peracids and oxaziridines have not been used for the oxidation of such substrates.
29. (a) Duffaut, N.; Calas, R ; Macé, J.-C. Bull. Chem. Soc. Fr. 1959, 1971-1973.
30. (b) Wiberg, E.; Amberger, E. In Hydrides of The Elements of Main Groups I-IV, Elsevier: Amsterdam, 1971; p 523.
31. (a) Nagai, Y.; Honda, K., Migita, T. J. Organomet. Chem. 1967, 8, 372-373.
32. (b) Sommer, L. H.; Arie Ulland, L.; Parker, G. A. J. Am. Chem. Soc. 1972, 94, 3469-3471.
33. (a) Ouellette, R. J.; Marks, D. L. J. Organomet. Chem. 1968, 11, 407-413.
34. (b) Spialter, L., Pazdernik, L.; Bernstein, S.; Swansiger, W. A.; Buell, G. R.; Freeburger, M E. J. Am. Chem. Soc. 1971, 93, 5682-5686.
35. (c) Dexheimer, E. M.; Spialter, L. J. Organomet. Chem. 1975, 102, 21-27.
36. (d) Corey, E. J.; Mehrotra, M. M., Khan, A. U. J. Am. Chem. Soc. 1986, 108, 2472-2473
37. (a) Al-Shali, S. A. I.; Eaborn, C.; Fattah, F. A.; Najim, S. T. J. Chem. Soc., Chem. Commun. 1984, 318-319.
38. (b) Ayoko, G. A.; Eaborn, C. J. Chem. Soc., Perkin Trans. 2 1987, 1047-1058.
39. (c) Lickiss, P. D.; Lucas, R. J. Organomet. Chem. 1995, 521, 229-234.
40. Adam, W ; Mello, R.; Curci, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 890-891.
41. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330.
42. Sommer, L. H., Lyons, J. E. J. Am. Chem. Soc. 1969, 91, 7061-7067.
43. (a) Matarasso-Tchiroukhine, E. J. Chem. Soc., Chem. Commun. 1990, 681-682.
44. (b) Egger, C.; Schubert, U. Z. Naturforsch 1991, 46b, 783-788.
45. (c) Schubert, U.; Lorenz, C. Inorg. Chem. 1997, 36, 1258-1259.
46. (a) Sommer, L. H.; Frye, C. L.; Parker, G. A.; Michael, K. W. J. Am Chem. Soc. 1964, 86, 3271-3276.
47. (b) Sommer, L. H ; McLick, J. J. Am. Chem. Soc. 1967, 89, 5806-5812.
48. (c) Sommer, L. H.; Michael, K. W.; Korte, W. D. J. Am. Chem. Soc. 1967, 89, 868-875.
49. (d) Corriu, R.; Royo, G. J. Organomet Chem 1968, 14, 291-307.
50. (e) Corriu, R.; Massé, J. Bull. Soc. Chim. Fr. 1969, 3491-3496.
51. (f) Sommer, L. H.; Rosborough, K. T. J. Am. Chem. Soc. 1969, 91, 7067-7076.
52. (g) Sommer, L. H.; Korte, W. D ; Frye, C. L J. Am. Chem. Soc. 1972, 94, 3463-3469.
53. Herrmann, W. A.; Kuchler, J. G.; Weichselbaumer, G.; Herdtweck, E.; Kiprof, P. J. Organomet. Chem. 1989, 372, 351-370.
54. Herrmann, W. A.; Fischer, R. W.; Scherer, W.; Rauch, M. U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1157-1160.
55. (a) Eaborn, C.; Walton, D. R. M. J. Chem. Soc. 1963, 5626-5632.
56. (b) Westermark, H. Acta Chem. Scand. 1955, 9, 947-954.
57. (a) Demuth, M.; Mikhail, G. Tetrahedron 1983, 39, 991-997.
58. (b) Larson, G. L.; del Valle, L. Synth. React. Inorg. Met.-Org. Chem. 1981, 11, 173-178.
59. (a) Gable, K. P. Adv. Organomet. Chem. 1997, 41, 127-161.
60. (b) Abu-Omar, M. M.; Hansen, P. J.; Espenson, J. H. J. Am. Chem. Soc. 1996, 118, 4966-4974.
61. (a) Schlenk, W. Chem. Unserer Zeit 1969, 121-127.
62. (b) Schlenk, W. Methoden Org. Chem. (Houben-Weyl) 1958, 1, 391-416.
63. (c) Harris, K. D. M. Chem. Soc. Rev. 1997, 26, 279-289.
64. (d) Müller, R.; Meier, G. Z. Anorg. Allg. Chem. 1964, 332, 81-94.
65. Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189-6190.
66. The condensation of silanol 2d to disiloxane 3d is catalyzed by complexes A and B and by one of the decomposition products of the MTO catalyst, e.g., perrhenate.
67. Mahdyarfar, A.; Harris, K. D. M. J. Chem. Soc., Chem. Commun. 1993, 51-53.
68. (a) Mikus, F. F.; Hixon, R. M.; Rundle, R. E. J. Am. Chem. Soc. 1946, 68, 1115-1133
69. (b) Allen, M. T.; Miola, L.; Suddaby, B. R.; Whitten, D. G. Tetrahedron 1987, 43, 1477-1484.
70. Hollingsworth, M. D.; Santarsiero, B. D.; Harris, K. D. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 649-652.
71. Force-field calculations reveal that the silane 1d fits inside the urea channels.
72. 2·HMPA: Hermann, W. A.; Correia, J. D. G.; Artus, G. R. J.; Fischer, R. W.; Romão, C. C. J. Organomet. Chem. 1996, 520, 139-142.
73. Camblor, M. A.; Corma, A.; García, H.; Semmer-Herlédan, V.; Valencia, S. J. Catal. 1988, 177, 267-272.
74. Hui, Y.; Russell, J. C.; Whitten, D. G. J. Am. Chem. Soc. 1983, 105, 1374-1376.
75. Suddaby, B. R.; Dominey, R. N.; Hui, Y.; Whitten, D. G. Can. J. Chem. 1985, 63, 1315-1319.
76. In some cases, the amylose additive turned yellow in the reaction mixture, which is due to the presence of the rhenium diperoxo complex B.
77. Herrmann, W. A.; Correia, J. D. G.; Kühn, F. E.; Artus, G. R. J.; Romão, C. C. Chem. Eur. J. 1996, 2, 168-173.
78. Peacock, R. D. In Comprehensive Inorganic Chemistry; Bailar, J. C., Emeléus, H. J., Nyholm, R., Trotman-Dickenson, A. F., Eds.; Pergamon Press: Oxford, 1973.