Trigermaallene and 1,3-digermasilaallene

Organometallics

Volumn 24, Issue 2, 2005, Pages 197-199

  Iwamoto, Takeaki ^a   Masuda, Hidenori ^a   Kabuto, Chizuko ^a   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHLORINE; CRYSTALLOGRAPHY; CRYSTALS; GERMANIUM; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

DYNAMIC DISORDER; GERMYLENE; METALLAALLENES; TRIGERMAALLENE;

ORGANIC COMPOUNDS;

EID: 12844275931     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049183e     Document Type: Article

References (41)

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15. Very recently, Sekiguchi et al. have reported the synthesis and isolation of the first disilyne: Sekiguchi, A.; Kinjo, R.; Ichinohe, M. Science 2004, 305, 1755.
16. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
17. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
18. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
19. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
20. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
21. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
22. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
23. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
24. For recent reviews of digermenes and germasilenes, see: (a) Driess, M.; Grutzmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828. (b) Baines, K.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. (c) Power, P. P. Chem. Rev. 1999, 99, 3463. (d) Escudie, J.; Ranaivonjatovo, H. Adv. Organomet. Chem. 1999, 44, 113. (e) Weiden-bruch, M. J. Organomet. Chem. 2002, 646, 39. (f) Tokitoh, N.; Okazaki, R. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; Vol. 2, Chapter 13, p 843. (g) Lee, V. Y.; Sekiguchi, A. In The Chemistry of Organic Germanium Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002, Vol. 2, Chapter 14, p 903. (h) Sekiguchi, A.; Lee, V. Y. Chem. Rev. 2003, 103, 1429. (i) Lee, V. Y.; Sekiguchi, A. Organometallics 2004, 23, 2822.
25. The syntheses of 1,3-disila-2-gallata- and 2-indataallenic anions have been reported: Nakata, N.; Izumi, R.; Lee, V. Y.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2004, 126, 5058.
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27. (b) Iwamoto, T.; Masuda, H.; Ishida, S.; Kabuto, C.; Kira, M. J. Organomet. Chem. 2004, 689, 1337.
28. Details of the insertion reactions of germylene 5 into M-X bonds (M = Si, Ge; X = Cl, Br) will be reported elsewhere. For the insertion of stable silylenes into Si-Cl bonds, see: (a) Ishida, S.; Iwamoto, T.; Kabuto, C.; Kira, M. Silicon Chem. 2003, 2, 137. (b) Moser, D. F.; Bosse, T.; Olson, J.; Moser, J. L.; Gusei, I. A.; West, R. J. Am. Chem. Soc. 2002, 124, 4186.
29. Details of the insertion reactions of germylene 5 into M-X bonds (M = Si, Ge; X = Cl, Br) will be reported elsewhere. For the insertion of stable silylenes into Si-Cl bonds, see: (a) Ishida, S.; Iwamoto, T.; Kabuto, C.; Kira, M. Silicon Chem. 2003, 2, 137. (b) Moser, D. F.; Bosse, T.; Olson, J.; Moser, J. L.; Gusei, I. A.; West, R. J. Am. Chem. Soc. 2002, 124, 4186.
30. max/nm (e)) 612 (3100), 488 (2500), 432 (3800), 383 (28 500).
31. 3; Z = 4; R1 = 0.047 (I > 2σ(I)); wR2 = 0.113 (all data); GOF = 1.03.
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35. Lee, V. Ya.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2000, 122, 12604.
36. The details of the estimation will be reported elsewhere.
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38. See the Supporting Information for the details of the theoretical calculations on 8B, 8Z, 9B, and 9Z.
39. 2 symmetry are given in the text.
40. γ planes are roughly reproduced. Details of the theoretical calculations will be reported elsewhere.
41. max/nm (ε) 584 (700) and 390 (21 300). In reality, the spectral pattern for 2 is rather similar to those for 3 and 4; three other bands for 2 are observed as shoulders. See the Supporting Information for details.