Reactivity of Dianionic Hexacoordinated Silicon Complexes toward Nucleophiles: A New Route to Organosilanes from Silica

Organometallics

Volumn 7, Issue 5, 1988, Pages 1165-1171

  Boudin, A ^a   Cerveau, G ^a   Chuit, C ^a   Corriu, R J P ^a   Reye, C ^a  

^a UNIV MONTPELLIER   (France)

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EID: 33845279280     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00095a023     Document Type: Article

References (56)

1. Boudin, A.; Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 474.
2. Rochow, E. G. J. Am. Chem. Soc. 1945, 67, 963. (b) An introduction to the chemistry of silicones, 2nd ed.; Wiley: New York, 1951; p 36.
3. Eaborn, C. Organosilicon Compounds; Butterworths: London, 1960; p 10.
4. Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79, 974. (b) Benkeser, R. A.; Cunico, R. F.; Dunny, S.; Jones, P. R.; Nerlekar, P. G. J. Org. Chem. 1967, 32, 2634.
5. Kautsky, H.; Bartocha, B. Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys., Biol. 1955, 10B, 422. (b) Fritz, G. Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem. Biophys. Biol. 1955, 10B, 423. (c) Wartmann, J.; Deuel, H. Helv. Chim. Acta 1959, 42, 1166. (d) Sleddon, G. J.; Anderson, R. C. Chem. Ind. 1960, 1335.
6. Rosenheim, A.; Raibmann, B.; Schendel, G. Z. Anorg. Allg. Chem. 1931, 196, 160.
7. Weiss, A.; Reiff, G.; Weiss, A. Z. Anorg. Allg. Chem. 1961, 311, 151. (b) Barnum, D. W. Inorg. Chem. 1970, 9, 1942; 1972, 11, 1424.
8. Corriu, R. J. P.; Cerveau, G.; Chuit, C.; Reye, C. Fr. Patent. 2575466, 1984.
9. Chu, H. K.; Johnson, M. D.; Frye, C. L. J. Organomet. Chem. 1984, 271, 327.
10. Muller, R. Z. Chem. 1984, 24, 41 and references cited therein.
11. Soshestvenskaya, E. M. Zh. Obshch. Khim. 1952, 22, 1122.
12. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132; 1965, 87, 21.
13. Dhar, S. K.; Doron, V.; Kirschner, S. J. Am. Chem. Soc. 1959, 81, 6372.
14. Inoue, T.; Fujita, J.; Saito, K. Bull. Chem. Soc. Jpn. 1975, 48, 1228.
15. Inoue, T. Inorg. Chem. 1983, 22, 2435.
16. Kummer, D.; Koster, H. Z. Anorg. Allg. Chem. 1973, 398, 279. (b) Kummer, D.; Koster, H. Z. Anorg. Allg. Chem. 1973, 402, 297. (c) Kummer, D.; Gaiper, K. E.; Seshadri, T. Chem. Ber. 1977, 110, 1950. (d) Kummer, D.; Seshadri, T. Z. Anorg. Allg. Chem. 1977, 428, 129.
17. Kummer, D.; Seshadri, T. Chem. Ber. 1977, 110, 2355.
18. Kummer, D.; Seshadri, T. Z. Anorg. Allg. Chem. 1977, 432, 147.
19. Tamao, K.; Yoshida, J.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Takahashi, M.; Kurita, A.; Murata, M.; Kumada, M. Organometallics 1982, 1, 355 and references cited therein. (b) Yoshida, J.; Tamao, K.; Kakui, T.; Kurita, A.; Murata, M.; Yamada, K.; Kumada, M. Organometallics 1982, 1, 369. (c) Yoshida, J.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542.
20. Boudin, A.; Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 473.
21. Corriu, R. J. P.; Guerin, C.; Henner, B. J. L.; Wong Chi Man, W. W. C. Organometallics 1988, 7, 237.
22. Boyer, J.; Breliere, C.; Corriu, R. J. P.; Kpoton, A.; Poirier, M.; Royo, G. J. Organomet. Chem. 1986, 311, C39.
23. Corriu, R. J. P. Proceedings of the Eighth International Organosilicon Symposium; Ellis Horwood Ltd: Chichester, England.
24. Corriu, R. J. P.; Dabosi, G.; Martineau, M. J. Chem. Soc., Chem. Commun. 1977, 649. (b) Corriu, R. J. P.; Dabosi, G.; Martineau, M. J. Organomet. Chem. 1978, 154, 33. (c) Corriu, R. J. P.; Dabosi, G.; Martineau, M. J. Organomet. Chem. 1980, 186, 25. (d) Corriu, R. J. P.; Guerin, C. Adv. Organomet. Chem. 1982, 20, 265.
25. Bassindale, A. R.; Stout, T. J. Organomet. Chem. 1982, 238, C41. (b) Chojnowski, J.; Cypryk, M.; Michalski, J. J. Organomet. Chem. 1978, 154, 33. (c) Chaudary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 99.
26. Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1983, 39, 999 and references cited therein.
27. Webster, O. W.; Hertler, W. R.; Sogah, D. Y.; Farnham, W. B.; Rajanbabu, T. V. J. Am. Chem. Soc. 1983, 105, 5706. (b) Sogah, D. Y.; Farnham, W. B. Organosilicon and Bioorganosilicon Chemistry; Sakurai, H., Ed.; Ellis Horwood Ltd: Chichester, England, 1985; p 219.
28. Weiss, A.; Herzog, A. In Biochemistry of Silicon and Related Problems; Bendz, G., Lindqvist, I., Eds.; Plenum: New York, 1978; p 109 and references cited therein.
29. Frye, C. L. J. Am. Chem. Soc. 1964, 86, 3170. (b) Frye, C. L. DP 1493601, 1964.
30. Bazhulin, P. A.; Egorov, Yu. P.; Mironov, V. F. Dokl. Akad. Nauk SSSR 1953, 92, 515.
31. Peake, J. S.; Nebergall, W. H.; Yun Ti Chen J. Am. Chem. Soc. 1952, 74, 1526.
32. Dolgov, B. M.; Khudobin, Yu. I.; Kharitonov, N. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1959, 1238; Chem. Abstr. 1960, 54, 1381.
33. Jenkins, J. W.; Lavery, N. L.; Guenther, P. R.; Post, H. W. J. Org. Chem. 1948, 13, 862.
34. Hughes, M. B. Diss. Abstr. 1959, 19, 1921.
35. Tannenbaum, S.; Kaye, S.; Lewenz, G. F. J. Am. Chem. Soc. 1953, 75, 3753.
36. Aston, J. G.; Kennedy, R. M.; Messerly, G. H. J. Am. Chem. Soc. 1941, 63, 2343.
37. Plate, A. F.; Belikova, N. A.; Egorov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1956, 1085; Chem. Abstr. 1957, 51, 5085.
38. West, R. J. Am. Chem. Soc. 1954, 76, 6012.
39. Gilman, H.; Clark, R. N. J. Am. Chem. Soc. 1947, 69, 967. (b) Gilman, H.; Marshall, F. I. J. Am. Chem. Soc. 1949, 71, 2066.
40. Whitmore, F. C.; Sommer, L. H.; Di Giorgio, P. A.; Strong, W. A.; Van Strien, R. E.; Bailey, D. L.; Hall, H. K.; Pietrusza, E. W.; Kerr, G. T. J. Am. Chem. Soc. 1946, 68, 475.
41. Rosenberg, S. D.; Walburn, J. J.; Strankovich, T. D.; Balint, A. E.; Ramsden, H. E. J. Org. Chem. 1957, 22, 1200.
42. Masson, J. C.; Le Quan Minh; Cadiot, P. Bull. Soc. Chim. Fr. 1968, 1085.
43. Maienthal, M.; Hellman, M.; Haber, C. P.; Hymo, L. A.; Carpenter, S.; Carr, A. J. J. Am. Chem. Soc. 1954, 76, 6392.
44. Spialter, L.; Priest, D. C.; Harris, C. W. J. Am. Chem. Soc. 1955, 77, 6227.
45. Curran, B. C.; Witucki, R. M.; McCusker, P. A. J. Am. Chem. Soc. 1950, 72, 4471.
46. Nebergall, W. H. J. Am. Chem. Soc. 1950, 72, 4702.
47. Larsson, E.; Van Gilse Van der Pals, E. Svensk Kemish Tidskrift 1951, 63, 179.
48. Calas, R.; Bourgeois, P. C.R. Seances Acad. Sci., Ser. C 1969, 268, 72.
49. Petrov, A. D.; Shchukovskaya, L. L.; Egorov, Yu. Dokl. Akad. Nauk SSR 1953, 93, 293; Chem. Abstr. 1954, 48, 13616.
50. Topchiev, A. V.; Nametkin, N. S.; Durgar'Yan, S. G. Zh. Obshch. Khim. 1960, 30, 927; Chem. Abstr. 1959, 53, 18894d.
51. Gilman, H.; Lichtenwalter, G. D. J. Am. Chem. Soc. 1958, 80, 608.
52. Benkeser, R. A.; Severson, R. G. J. Am. Chem. Soc. 1951, 73, 1424.
53. Gilman, H.; Gerow, C. W. J. Am. Chem. Soc. 1956, 78, 5435.
54. Kraus, C. A.; Nelson, W. K. J. Am. Chem. Soc. 1934, 56, 195.
55. Voronkov, M. G.; Yakubovskaya, A.Y.A. Zh. Obshch. Khim. 1955, 25, 1124; Chem. Abstr. 1956, 50, 3217.
56. Finholt, A. E.; Bond, A. C., Jr.; Wilzbach, K. E.; Schlesinger, H. I. J. Am. Chem. Soc. 1947, 69, 2692.