Phosphonium chloride induced dichlorosilylene transfer from trichlorosilane

Organometallics

Volumn 22, Issue 13, 2003, Pages 2551-2553

  Kang, Seung Hyun ^a,b   Han, Joon Soo ^a   Lee, Myong Euy ^b   Yoo, Bok Ryul ^a   Jung, Il Nam ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CHARGE TRANSFER; CHEMICAL ACTIVATION; HYDROCHLORIC ACID; MOLECULAR STRUCTURE; SOLUTIONS; SUBSTRATES; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

DICHLOROSILYLENE; PHOSPHONIUM CHLORIDE; TRICHLOROSILANE;

SILANES;

EID: 0038538242     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0302488     Document Type: Article

References (34)

1. Nefedov, O. M.; Manakov, M. N. Angew. Chem., Int. Ed. Engl. 1966, 5, 1021.
2. (b) Atwell, W. H.; Weyenberg, D. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 469.
3. (c) Gaspar, P. P.; West, R. In The Chemistry of Organosilicon Compounds; Wiley: New York, 1998; Vol. II, pp 2463-2568.
4. Gaspar, P. P. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1978, Vol. I, pp 229-277.
5. Gaspar, P. P. Ibid., Vol. II, pp 335-385.
6. (a) Sirtl, E.; Reuschel, K. Z. Anorg. Allg. Chem. 1964, 332, 113.
7. (b) Chernyshev, E. A.; Komalenkova, N. G.; Bashkirova, S. A. J. Organomet. Chem. 1984, 271, 129.
8. (c) Walker, K. L.; Jardine, R. E.; Ring, M. A.; O'Neal, H. E. Int. J. Chem. Kinet. 1998, 30, 69.
9. Wilkins, C. J. J. Chem. Soc. 1953, 3409.
10. (a) Benkeser, R. A. Acc. Chem. Res. 1971, 4, 94.
11. (b) Benkeser, R. A.; Smith, W. E. J. Am. Chem. Soc. 1968, 90, 5307.
12. (c) Benkeser, R. A.; Gaul, J. M.; Smith, W. E. J. Am. Chem. Soc. 1969, 91, 3666.
13. Karsch, H. H.; Schlüter, P. A.; Bienlein, F.; Herker, M.; Witt, E.; Sladek, A.; Heckel, M. Z. Anorg. Allg. Chem. 1998, 624, 295.
14. (a) de Mont, W.-W.; Gust, T.; Seppälä, E.; Wismach, C.; Jones, P. G.; Ernst, L.; Gruneneberg, J.; Marsmann, H. C. Angew. Chem., Int. Ed. 2002, 41, 3829.
15. (b) de Mont, W.-W.; Müller, L.; Martens, R.; Papathomas, P. M.; Smart, B. A.; Robertson, H. E.; Rankin, D. W. H. Eur. J. Inorg. Chem. 1999, 1381.
16. (a) Cho, Y. S.; Kang, S.-H.; Han, J. S.; Yoo, B. R.; Jung, I. N. J. Am. Chem. Soc. 2001, 123, 5584.
17. (b) Kang, S.-H.; Han, J. S.; Yoo, B. R.; Lee, M. E.; Jung, I. N. Organometallics 2003, 22, 529.
18. (a) Timms, P. L. Inorg. Chem. 1968, 7, 387.
19. (b) Chernyshev, E. A.; Komalenkova, N. G.; Kapitova, L. A.; Bashkirova, S. A. Zh. Obshch. Khim. 1996, 66, 1141.
20. (c) Ishida, S.; Iwamoto, T.; Kabuto, C.; Kira, M. Chem. Lett. 2001, 1102.
21. (d) Moser, D. F.; Bosse, T.; Olson, J.; Moser, J. L.; Guzei, I. A.; West, R. J. Am. Chem. Soc. 2002, 124, 4186.
22. 3) δ 23.10, 23.74, 27.00, 123.03, 138.73. Data for other minor products and the reactions with 1a,c-e in detail are described in the Supporting Information.
23. Barton, T. J.; Tillman, N. J. Am. Chem. Soc. 1987, 109, 6711.
24. 1,4-Bis(trichlorosilyl)-2,3-dimehtylbut-3-enes obtained as minor products from a reaction of 1c with trichlorosilane were characterized indirectly by comparing the NMR spectra of their methylation products with those in the following reference: Dunogues, J.; Calas, R.; Dedier, J.; Pisciotti, F. J. Organomet. Chem. 1970, 25, 51. Data for the methylation of 2c in detail are given in the Supporting Information.
25. Damrauer, R.; Simon, R.; Laporterie, A.; Manuel, G.; Park, Y. T.; Weber, W. P. J. Organomet. Chem. 1990, 391, 7.
26. Chernyshev, E. A.; Komalenkova, N. G.; Yakovleva, G. N.; Bykovenko, V. G.; Shcherbinin, V. V.; Belokon, A. I. Zh. Obshch. Khim. 2001, 71, 1438.
27. The geometric structure for 2d was characterized indirectly by comparing the NMR spectra of the methylation products with those in the following reference: Lei, D.; Hwang, R.-J.; Gaspar, P. P. J. Organomet. Chem. 1984, 271, 1. Data for the methylation of 2d in detail are given in the Supporting Information.
28. 2Si: C, 62.95; H, 4.62. Found: C, 63.21; H, 4.69.
29. Furuya, N.; Sukawa T. J. Organomet. Chem. 1975, 96, C1.
30. Wiberg, N.; Niedermayer, W. J. Organomet. Chem. 2001, 628, 57.
31. Hexachlorodisilane decomposed into tetrachlorosilane and polysilanes in the presence of tetrabutylphosphonium chloride at the reaction temperatures.
32. (a) Atwell, W. H.; Weyenburg, D. R. J. Organomet. Chem. 1966, 5, 5940.
33. (b) Atwell, W. H.; Weyenburg, D. R. J. Am. Chem. Soc. 1968, 90, 3438.
34. 2: C, 39.78; H, 5.56. Found: C, 39.85; H, 5.59. For data of other minor products and the X-ray structure of compound 3, see the Supporting Information. The Cambridge Crystallographic Data Base file CCDC 200443 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K., fax (+44) 1223-336-033, e-mail deposit@ccdc.cam.ac.uk).