Siletanylmethyllithium: An ambiphilic organosilane

Chemical Communications

Volumn , Issue 24, 2005, Pages 3047-3049

  Kozytska, Mariya V ^a   Dudley, Gregory B ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; ORGANOSILANE DERIVATIVE; SILANE DERIVATIVE; SILETANYLMETHYLLITHIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; REACTION ANALYSIS;

EID: 21844449474     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503110a     Document Type: Article

References (30)

1. S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 2002, 35, 835.
2. R. Damrauer, A. J. Crowell and C. F. Craig, J. Am. Chem. Soc., 2003, 125, 10759.
3. (a) A. G. Myers, S. E. Kephart and H. Chen, J. Am. Chem. Soc., 1992, 114, 7922;
4. (b) S. E. Denmark, B. D. Griedel, D. M. Coe and M. E. Schnute, J. Am. Chem. Soc., 1994, 116, 7026.
5. (a) K. Matsumoto, K. Oshima and K. Utimoto, J. Org. Chem, 1994, 59, 7152;
6. (b) K. Omoto, Y. Sawada and H. Fujimoto. J. Am. Chem. Soc., 1996, 118, 1750.
7. For examples and leading references, see: (a) K. Matsumoto, H. Shimazu, M. Deguchi and H. Yamaoka, J. Polym. Sci. Part A: Polym. Chem., 1997, 35, 3207;
8. (b) R. Knischka, H. Frey, U. Rapp and F. J. Mayer-Posner, Macromol. Rapid Commun., 1998, 19, 455;
9. (c) R. K. Sheikh, K. Tharanikkarasu, I. Imae and Y. Kawakami, Macromolecules, 2001, 34, 4384.
10. (a) S. E. Denmark and J. Y. Choi, J. Am. Chem. Soc., 1999, 121, 5821;
11. (b) S. E. Denmark and Z. Wang, Synthesis, 2000, 999.
12. J. D. Sunderhaus, H. Lam and G. B. Dudley, Org. Lett. 2003, 5, 4571.
13. (a) A. Pelter, Pure Appl. Chem., 1994, 66, 223;
14. (b) T. Kawashima, N. Yamashita and R. Okazaki, J. Am. Chem. Soc., 1995, 117, 6142.
15. D. J. Ager, Org. React., 1990, 38, 1.
16. W. C. Kaska, Coord. Chem. Rev., 1983, 48, 1.
17. (a) Commercially available from Aldrich;
18. (b) N. Auner and J. Grobe, J. Organomet. Chem., 1980, 188, 25.
19. For coupling of 3 with an alkyny/lithium (lithium acetylide), see ref. 6a.
20. D. Seyferth and E. G. Rochow, J. Org. Chem., 1955, 20, 250.
21. (a) E. Fillion and N. J. Taylor, J. Am. Chem. Soc., 2003, 125, 12700;
22. (b) T. Kauffmann and R. Kriegesmann, Chem. Ber., 1982, 115, 1810.
23. D. E. Seitz, J. J. Carroll, C. P. Cartaya M., S.-H. Lee and A. Zapata, Synth. Commun., 1983, 13, 129.
24. H. J. Reich and N. H. Phillips, J. Am. Chem. Soc., 1986, 108, 2102.
25. B. E. Maryanoff and A. B. Reitz, Chem. Rev., 1989, 89, 863.
26. The two-step Peterson olefination of benzophenone using the trimethylsilyl analog of 1 is known: D. E. Seitz and A. Zapata, Tetrahedron Lett., 1980, 21, 3451.
27. For computational studies on siletane electrophilicity, see refs. 2 and 4b.
28. We are unable to conclude at this time if decomposition (B → 9) occurs before or after aqueous quench. In situ spectroscopy studies that may elucidate this detail will be reported in due course.
29. For relevant examples, see: (a) P. A. Brough, S. Fisher, B. Zhao, R. C. Thomas and V. Snieckus, Tetrahedron Lett., 1996, 37, 2915;
30. (b) K. Itami, T. Kamei, K. Mitsudo, T. Nokami and J. Yoshida, J. Org. Chem., 2001, 66, 3970.