Synthesis of unsymmetrically substituted cyclotrigermenes and the first example of cis configuration around the Ge=Ge double bond [11]

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11587-11588

  Sekiguchi, Akira ^a   Fukaya, Norihisa ^a   Ichinohe, Masaaki ^a   Takagi, Nozomi ^b   Nagase, Shigeru ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKENE; GERMANIUM DERIVATIVE;

CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033573068     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9923080     Document Type: Letter

References (41)

1. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
2. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
3. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
4. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
5. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
6. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
7. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, 39 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
8. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
9. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
10. 2 (M = Si, Ge, Sn), see: (a) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (b) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (c) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (d) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Chem. Chem. Rev. 1994, 130, 427. (e) Baines, K. M.; Stibbs, W. G. Coord. Chem. Rev. 1995, 145, 157. (f) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 231. (g) Baines, K. M.; Stibhs, W. G. Adv. Organomet. Chem. 1996, A 275. (h) Raabe. G.; Michl, J. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Ltd.: New York, 1989; Part 2. Chapter 17. (i) Sakurai, H. The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons Ltd.: New York, 1998; Vol. 2, Part 1, Chapter 15. (j) Weidenbruch. M. Eur. J. Inorg. Chem. 1999, 373.
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21. 2. The structure of 2e was also characteri/ed by X-ray crystallography.
22. 7: C, 50.81; H, 10.23. Found: C, 50.62; H, 9.94.
23. o) (Rw = 0.142 for all data, 8618 reflections).
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39. For crystal structures of digermenes, see: (a) Snow, J. T.; Murakami, S.; Masamune, S.; Williams, D. J. Tetrahedron Lett. 1984, 25, 4191. (b) Hitchcock, P. B.; Lappert, M. F.; Miles, S. J.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 480. (c) Goldberg, D. E.; Hitchcock, P. B.; Lappert, M. F.; Thomas, K. M.; Thorne, A. J.; Fjeldberg, T.; Haaland, A.; Schilling, B. E. R. J. Chem. Soc., Dalton Trans. 1986, 2387. (d) Batcheller, S. A.; Tsumuraya, T.; Tempkin, O.; Davis, W. M.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 9394. (d) Weidenbruch, M.; Stürmann, M.; Kilian, H.; Pohl, S.; Saak. W. Chem. Ber. 1997, 130, 735.
40. For crystal structures of digermenes, see: (a) Snow, J. T.; Murakami, S.; Masamune, S.; Williams, D. J. Tetrahedron Lett. 1984, 25, 4191. (b) Hitchcock, P. B.; Lappert, M. F.; Miles, S. J.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 480. (c) Goldberg, D. E.; Hitchcock, P. B.; Lappert, M. F.; Thomas, K. M.; Thorne, A. J.; Fjeldberg, T.; Haaland, A.; Schilling, B. E. R. J. Chem. Soc., Dalton Trans. 1986, 2387. (d) Batcheller, S. A.; Tsumuraya, T.; Tempkin, O.; Davis, W. M.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 9394. (d) Weidenbruch, M.; Stürmann, M.; Kilian, H.; Pohl, S.; Saak. W. Chem. Ber. 1997, 130, 735.
41. Kira, M.; Iwamoto, T.; Maruyama, T.; Kabuto, C.; Sakurai, H. Organometallics 1996, 15, 3767.