The first silastannene 〉Si=Sn〈: A new doubly-bonded system of heavier group 14 elements

Journal of the American Chemical Society

Volumn 124, Issue 50, 2002, Pages 14822-14823

  Sekiguchi, Akira ^a   Izumi, Rika ^a   Lee, Vladimir Ya ^a   Ichinohe, Masaaki ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SILICON; TIN;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS;

EID: 0037132578     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021077l     Document Type: Article

References (30)

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5. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
6. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
7. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
8. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. Inorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
9. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
10. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
11. For the recent reviews on metallenes and dimetallenes of group 14 elements, see: (a) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (b) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (c) Kaftory, M.; Kapon, M.; Botoshansky, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 5. (d) Weidenbruch, M. Eur. J. lnorg. Chem. 1999, 373. (e) Power, P. P. Chem. Rev. 1999, 99, 3463. (f) Escudié, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (g) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y. Eds.; John Wiley & Sons Ltd.: New York, 2001; Vol. 3, Chapter 5.
12. For other examples of heteronuclear dimetallenes of heavier group 14 elements, which were stable only at low temperatures and were characterized by low-temperature NMR spectra and trapping reactions without isolation: For germasilene, see: (a) Baines, K. M.; Cooke, J. A. Organometallics 1991, 10, 3419. (b) Baines, K. M.; Cooke, J. A. Organometallics 1992, 11, 3487. For germastannene, see: (c) Chaubon, M.-A.; Escudié, J.; Ranaivonjatovo, H.; Satgé, J. J. Chem. Soc., Chem. Commun. 1996, 2621.
13. For other examples of heteronuclear dimetallenes of heavier group 14 elements, which were stable only at low temperatures and were characterized by low-temperature NMR spectra and trapping reactions without isolation: For germasilene, see: (a) Baines, K. M.; Cooke, J. A. Organometallics 1991, 10, 3419. (b) Baines, K. M.; Cooke, J. A. Organometallics 1992, 11, 3487. For germastannene, see: (c) Chaubon, M.-A.; Escudié, J.; Ranaivonjatovo, H.; Satgé, J. J. Chem. Soc., Chem. Commun. 1996, 2621.
14. For other examples of heteronuclear dimetallenes of heavier group 14 elements, which were stable only at low temperatures and were characterized by low-temperature NMR spectra and trapping reactions without isolation: For germasilene, see: (a) Baines, K. M.; Cooke, J. A. Organometallics 1991, 10, 3419. (b) Baines, K. M.; Cooke, J. A. Organometallics 1992, 11, 3487. For germastannene, see: (c) Chaubon, M.-A.; Escudié, J.; Ranaivonjatovo, H.; Satgé, J. J. Chem. Soc., Chem. Commun. 1996, 2621.
15. For 2-disilagermirene with a Si=Ge double bond, see: Lee, V. Ya.; Ichinohe, M.; Sekiguchi, A.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2000, 122, 9034.
16. Lee, V. Ya.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2000, 122, 12604.
17. Sekiguchi, A.; Ichinohe, M.; Yamaguchi, S. J. Am. Chem. Soc. 1999, 121, 10231.
18. Ichinohe, M.; Arai, Y.; Sekiguchi, A.; Takagi, N.; Nagase. S. Organometallics 2001, 20, 4141.
19. To our knowledge, there is only one paper in which the intermediate formation of a compound with a Si=Sn double bond was suggested. Drost, C.; Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F. Chem. Commun. 1997, 1845. However, neither spectroscopic nor chemical reactivity evidence was given to prove this structure.
20. Masamune, S.; Sita, L. R. J. Am. Chem. Soc. 1985, 107, 6390.
21. 3Sn: C, 66.41; H, 10.22. Found: C, 66.11; H, 10.00.
22. 119Sn NMR resonances of doubly bonded Sn atoms lie in the region above +400 ppm, see ref 4a.
23. 29Si NMR resonances for doubly bonded Si atoms lie in the region of +49 to +155 ppm, see ref 4b.
24. o) (Rw = 0.1630 for all data 12279 reflections), GOF = 1.024.
25. See ref 4c and also: Schmedake, T. A.; Haaf, M.; Apeloig, Y.; Müller, T.; Bukalov, S.; West, R. J. Am. Chem. Soc. 1999, 121, 9479.
26. Mackay, K. M. In The Chemistry of Organic Germanium, Tin and Lead Compounds; Patai, S., Ed.; John Wiley & Sons Ltd.: New York, 1995; Chapter 2.
27. The electronegativities of Si and Sn atoms according to the Pauling and the Allred - Rochow electronegativity scales are 1.90 vs 1.96 and 1.90 vs. 1.93, respectively.
28. The structure on the bottom in Scheme 2 represents an extreme case of such interaction with a planar geometry around a positively polarized Sn atom and 90° bending geometry around a negatively polarized Si atom.
29. The calculations were carried out using the Gaussian 98 program.
30. For the experimental procedures and spectral data of 3 and 4, see the Supporting Information.