Efficient and rapid C-Si bond cleavage in supercritical water

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6058-6059

  Itami, Kenichiro ^a   Terakawa, Koji ^a   Yoshida, Jun ichi ^a   Kajimoto, Okitsugu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; POLYMER; SILICON; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DIELECTRIC CONSTANT; PRESSURE; PROTON TRANSPORT; SILYLATION; SUPERCRITICAL FLUID; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 0038288844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034227g     Document Type: Article

References (24)

1. (a) Kajimoto, O. Chem. Rev. 1999, 99, 355.
2. (b) Savage, P. E. Chem. Rev. 1999, 99, 603.
3. (c) Bröll, D.; Kaul, C.; Krämer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998.
4. (d) Siskin, M.; Katrinzky, A. R. Chem. Rev. 2001, 101, 825.
5. Selected examples. Diels-Alder reaction: (a) Korzenski, M. B.; Kolis, J. W. Tetrahedron Lett. 1997, 38, 5611.
6. (b) Harano, Y.; Sato, H.; Hirata, F. J. Am. Chem. Soc. 2000, 122, 2289.
7. Friedel-Crafts alkylation: (c) Chandler, K.; Deng, F.; Dillow, A. K.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 1997, 36, 5175.
8. Beckmann and pinacol rearrangements: (d) Ikushima, Y.; Hatakeda, K.; Sato, O.; Yokoyama, T.; Arai, M. J. Am. Chem. Soc. 2000, 122, 1908. Ester hydrolysis:
9. (e) Oka, H.; Yamago, S.; Yoshida, J.; Kajimoto, O. Angew. Chem., Int. Ed. 2002, 41, 623.
10. Pdcatalyzed Mizoroki-Heck reaction: (f) Reardon, P.; Metts, S.; Crittendon, C.; Daugherity, P.; Parsons, E. J. Organometallics 1995, 14, 3810.
11. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000.
12. Eaborn, C. Pure Appl. Chem. 1969, 19, 375.
13. To exclude any positive or negative effect of the stainless steel reactor, most of the reactions in this study were performed in a sealed quartz tube placed in a stainless steel reactor (SUS316).
14. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. 1989, 37, 57.
15. 2O (390 °C), complete isomerization into inner alkenes was observed within 3 h.
16. (a) Reference 6.
17. (b) Laguerrf, M.; Grignon-Dubois, M.; Dunoguès, J. Tetrahedron 1981, 37, 1161.
18. Utimoto, K.; Kitai, M.; Nozaki, H. Tetrahedron Lett. 1975, 2825.
19. (a) Kumada, M.; Tamao, K.; Yoshida, J. J. Organomet. Chem. 1982, 239, 115.
20. (b) Tamao, K. Advances in Silicon Chemistry; JAI Press Inc.: Greenwich, CT, 1996; Vol. 3, p 1.
21. Armitage, D. A. In Comprehensive Orgamometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 2, Chapter 9.1. Armitage has noted in this comprehensive review: "Tetraalkylsilanes are remarkably stable compounds. The silicon-carbon bond is strong and almost nonpolar. It is therefore only broken under the most vigorous conditions, unless assisted by an alkyl group possessing an activating substituent suitably placed." Representative methods of C-Si bond cleavage of tetraalkylsilane are collected in this review. For relatively recent examples on this subject, see: Kakiuchi, F.; Furuta, K.; Murai, S.; Kawasaki, Y. Organometallics 1993, 12, 15. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
22. Armitage, D. A. In Comprehensive Orgamometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 2, Chapter 9.1. Armitage has noted in this comprehensive review: "Tetraalkylsilanes are remarkably stable compounds. The silicon-carbon bond is strong and almost nonpolar. It is therefore only broken under the most vigorous conditions, unless assisted by an alkyl group possessing an activating substituent suitably placed." Representative methods of C-Si bond cleavage of tetraalkylsilane are collected in this review. For relatively recent examples on this subject, see: Kakiuchi, F.; Furuta, K.; Murai, S.; Kawasaki, Y. Organometallics 1993, 12, 15. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
23. Armitage, D. A. In Comprehensive Orgamometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 2, Chapter 9.1. Armitage has noted in this comprehensive review: "Tetraalkylsilanes are remarkably stable compounds. The silicon-carbon bond is strong and almost nonpolar. It is therefore only broken under the most vigorous conditions, unless assisted by an alkyl group possessing an activating substituent suitably placed." Representative methods of C-Si bond cleavage of tetraalkylsilane are collected in this review. For relatively recent examples on this subject, see: Kakiuchi, F.; Furuta, K.; Murai, S.; Kawasaki, Y. Organometallics 1993, 12, 15. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
24. When the reaction was performed directly in a stainless reactor, desilylation was quite inefficient (57% conversion; dodecane 19%; 5 29%). Therefore, in this particular class of compounds (tetraalkylsilanes), the inhibiting effect of the stainless steel reactor (SUS316) and/or the promoting effect of the quartz tube might be involved for C-Si bond cleavage.