Silyl-substituted 1,4-disila(Dewar benzene): New synthesis and unexpected insertion of CO into the Si-Si bond to form a disilyl ketone

Organometallics

Volumn 24, Issue 14, 2005, Pages 3368-3370

  Nakata, Norio ^a   Oikawa, Toru ^a   Matsumoto, Takeshi ^a   Kabe, Yoshio ^a   Sekiguchi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; CARBON MONOXIDE; CHEMICAL BONDS; DERIVATIVES; ISOMERIZATION; PHOTOLYSIS; SILICON; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

DEWAR BENZENE; DISILYL KETONE; INTRAMOLECULAR ISOMERIZATION; SILICON ATOMS;

KETONES;

EID: 22444434578     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050261n     Document Type: Article

References (35)

1. For reviews of silaaromatic compounds, see: (a) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 1102-1108.
2. (b) Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; pp 151-166.
3. (c) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: New York, 1998; Vol. 2, Chapter 1.
4. (d) Tokitoh, N. Acc. Chem. Res. 2004, 37, 86.
5. (a) Wakita, K.; Tokitoh, N.; Okazaki, R.; Nagase, S. Angew. Chem., Int. Ed. 2000, 39, 634.
6. (b) Wakita, K.; Tokitoh, N.; Okazaki, R.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2000, 122, 5648.
7. (a) Tokitoh, N.; Wakita, K.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1997, 119, 6951.
8. (b) Wakita, K; Tokitoh, N.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1999, 121, 11336.
9. (c) Wakita, K.; Tokitoh, N.; Okazaki, R. Bull. Chem. Soc. Jpn. 2000, 73, 2157.
10. (d) Takeda, N.; Shinohara, A.; Tokitoh, N. Organometallics 2002, 21, 4024.
11. (a) Takeda, N.; Shinohara, A.; Tokitoh, N. Organometallics 2002, 21, 256.
12. (b) Shinohara, A.; Takeda, N.; Tokitoh, N. J. Am. Chem. Soc. 2003, 125, 10804.
13. Maier, G.; Schottler, K.; Reisenauer, H. P. Tetrahedron Lett. 1985, 26, 4039.
14. (a) Rich, J. D.; West, R. J. Am. Chem. Soc. 1982, 104, 6884.
15. (b) Welsh, K. M.; Rich, J. D.; West, R. J. Organomet. Chem. 1987, 325, 105.
16. Kabe, Y.; Ohkubo, K.; Ishikawa, H.; Ando, W. J. Am. Chem. Soc. 2000, 122, 3775.
17. Priyakumar, U. D.; Punnagai, M.; Sastry, G. N. J. Organomet. Chem. 2004, 689, 1284.
18. For the experimental procedures and spectral data of 1-4, see the Supporting Information.
19. Kang, S. H.; Han, J. S.; Lee, M. E.; Yoo, B. R.; Jung, I. N. Organometallics 2003, 22, 2551.
20. max = 50.00°, R1 (I > 2σ(I)) = 0.0669, wR2 (all data) = 0.2019 for 10 937 reflections and 649 parameters, GOF = 1.063.
21. Priyakumar, U. D.; Saravanan, D.; Sastry, G. N. Organometallics 2002, 21, 4823.
22. (a) Weinges, K.; Kasel, W.; Huber-Patz, U.; Rodewald, H.; Irngartinger, H. Chem. Ber. 1984, 117, 1868.
23. (b) Weinges, K.; Klein, J.; Sipos, W.; Günther, P.; Huber-Patz, U.; Rodewald, H.; Deuter, J.; Irngartinger, H. Chem. Ber. 1986, 119, 1540.
24. (c) Weinges, K.; Sipos, W.; Klein, J.; Deuter, J.; Irngartinger, H. Chem. Ber. 1987, 120, 5.
25. (d) Hanamoto, T.; Koga, Y.; Kawanami, T.; Furuno, H.; Inanaga, J. Angew. Chem., Int. Ed. 2004, 43, 3582.
26. (a) Brook, A. G.; Jones, P. F.; Peddle, G. J. D. Can. J. Chem. 1968, 46, 2119.
27. (b) Ricci, A.; Fiorenza, M.; Degl'Innocenti, A.; Seconi, G.; Dembech, P.; Witzgall, K.; Bestmann, H. J. Angew. Chem., Int. Ed. Engl. 1985, 24, 1068.
28. (c) Sakurai, H.; Yamane, M.; Iwata, M.; Saito, N.; Narasaka, K. Chem. Lett. 1996, 841.
29. (d) Pan, M.; Benneche, T. Synth. Commun. 1998, 28, 1415.
30. (e) Narasaka, K.; Saio, N.; Hayashi, Y.; Ichida, H. Chem. Lett. 1990, 1411.
31. Silverstein, R. M.; Bassler, G. C.; Morril, T. C. In Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991.
32. Brook, A. G.; Abdesaken, F.; Gutekunst, G.; Plavac, N. Organometallics 1982, 1, 994.
33. max = 55.96°, R1 (I > 2σ(I)) = 0.0436, wR2 (all data) = 0.1254 for 8053 reflections and 427 parameters, GOF = 1.029.
34. (a) Plummer, B. F.; Currey, J. A.; Russell, S. J.; Steffen, L. K.; Watson, W. H.; Bourne, S. A. Struct. Chem. 1995, 6, 167.
35. (b) Zhang, J.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 2001, 123, 10919.