SHi Reactions at Silicon as Unimolecular Chain Transfer Steps in the Formation of Cyclic Alkoxysilanes

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 462-465

  Studer, Armido ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Radical reactions; Silicon; Silyl ethers; Tin

Indexed keywords

EID: 0032473518     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980302)37:4<462::AID-ANIE462>3.0.CO;2-M     Document Type: Article

References (37)

1. D. P. Curran, Synthesis 1988, 489; D. H. R. Barton, M. Ramesh, J. Am. Chem. Soc. 1990, 112, 891; D. P. Curran, E. Eichenberger, M. Collis, M. G. Roepel, G. Thoma, ibid. 1994, 116, 4279; D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos, R. I. Walter, ibid. 1994, 116, 8937.
2. D. P. Curran, Synthesis 1988, 489; D. H. R. Barton, M. Ramesh, J. Am. Chem. Soc. 1990, 112, 891; D. P. Curran, E. Eichenberger, M. Collis, M. G. Roepel, G. Thoma, ibid. 1994, 116, 4279; D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos, R. I. Walter, ibid. 1994, 116, 8937.
3. D. P. Curran, Synthesis 1988, 489; D. H. R. Barton, M. Ramesh, J. Am. Chem. Soc. 1990, 112, 891; D. P. Curran, E. Eichenberger, M. Collis, M. G. Roepel, G. Thoma, ibid. 1994, 116, 4279; D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos, R. I. Walter, ibid. 1994, 116, 8937.
4. D. P. Curran, Synthesis 1988, 489; D. H. R. Barton, M. Ramesh, J. Am. Chem. Soc. 1990, 112, 891; D. P. Curran, E. Eichenberger, M. Collis, M. G. Roepel, G. Thoma, ibid. 1994, 116, 4279; D. Crich, C. Chen, J.-T. Hwang, H. Yuan, A. Papadatos, R. I. Walter, ibid. 1994, 116, 8937.
5. J. T. Banks, H. Garcia, M. A. Miranda, J. Pérez-Prieto, J. C. Scaiano, J. Am. Chem. Soc. 1995, 117, 5049.
6. M. C. Fong, C. H. Schiesser, Aust. J. Chem. 1992, 45, 475.
7. C. H. Schiesser, L. M. Wild, Tetrahedron 1996, 52, 13 265.
8. C. H. Schiesser, M. L. Styles, L. M. Wild, J. Chem. Soc. Perkin Trans. 2 1996, 2257.
9. K. J. Kulicke, C. Chatgilialoglu, B. Kopping, B. Giese, Helv. Chim. Acta 1992, 75, 935.
10. K. Miura, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1993, 66, 2348.
11. a) D. P. Curran, J. Xu, E. Lazzarini, J. Chem. Soc. Perkin Trans. 1 1995, 3049;
12. b) D. P. Curran, J. Xu, ibid. 1995, 3061;
13. c) A. Martinez-Grau, D. P. Curran, J. Org. Chem. 1995, 60, 8332:
14. d) D. P. Curran, J. Xu, E. Lazzarini, J. Am. Chem. Soc. 1995, 117, 6603;
15. e) A. Martinez-Grau, D. P. Curran, Tetrahedron 1997, 53, 5679.
16. For other UMCT reactions see: f) G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
17. For other UMCT reactions see: f) G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
18. For other UMCT reactions see: f) G. E. Keck, E. J. Enholm, J. B. Yates, M. R. Wiley, Tetrahedron 1985, 41, 4079; S. Kim, J. S. Koh, J. Chem. Soc. Chem. Commun. 1992, 1377; J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc. 1992, 114, 7909.
19. G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
20. [12] and 2-iodobenzyl alcohol (85%).
21. M. Murakami, M. Suginome, K. Fujimoto, H. Nakamura, P. G. Andersson, Y. Ito, J. Am. Chem. Soc. 1993, 115, 6487.
22. A. Kawachi, N. Doi, K. Tamao, J. Am. Chem. Soc. 1997, 119, 233.
23. Compilation of Si - Si bond energies: R. Walsh, Acc. Chem. Res. 1981, 14, 246.
24. M. Harendza, J. Junggebauer, K. Lessmann, W. P. Neumann, H. Tews, Synlett 1993, 286.
25. S. J. Cole, J. N. Kirwan, B. P. Roberts, C. R. Willis, J. Chem. Soc. Perkin Trans 1 1991, 103. See also C. Chatgilialoglu, K. U. Ingold, J. C. Scaiano, J. Am. Chem. Soc. 1983, 105, 3292.
26. S. J. Cole, J. N. Kirwan, B. P. Roberts, C. R. Willis, J. Chem. Soc. Perkin Trans 1 1991, 103. See also C. Chatgilialoglu, K. U. Ingold, J. C. Scaiano, J. Am. Chem. Soc. 1983, 105, 3292.
27. M. F. Lappert, J. B. Pedley, J. Simpson, T. R. Spalding, J. Organomet. Chem. 1971, 29, 195.
28. D. P. Curran, M.-H. Chen, D. Kim, J. Am. Chem. Soc. 1989, 111, 6265.
29. So far the origin of the reduction product is not clear. When the UMCT reaction was conducted under higher dilution (0.01M) no reduction product 11 was observed: however, unidentified side products were formed.
30. 3SnH did not provide better results.
31. Interestingly, the presence of the reduction product in analogy to the formation of 11 could not be observed.
32. The mediocre yield is due to partial decomposition of the products during chromatography.
33. The diastereoisomers could not be separated. We could not determine which isomer was formed in excess.
34. The relative configuration was assigned by NOE experiments.
35. L. J. Benja min, C. H. Schiesser, K. Sutej, Tetrahedron 1993, 49, 2557; D. Colombani, B. Maillard, ibid. 1996, 52, 14855. Other stereoselective UMCT reactions: D. P. Curran, J. Xu, Synlett 1997, 1102.
36. L. J. Benja min, C. H. Schiesser, K. Sutej, Tetrahedron 1993, 49, 2557; D. Colombani, B. Maillard, ibid. 1996, 52, 14855. Other stereoselective UMCT reactions: D. P. Curran, J. Xu, Synlett 1997, 1102.
37. L. J. Benja min, C. H. Schiesser, K. Sutej, Tetrahedron 1993, 49, 2557; D. Colombani, B. Maillard, ibid. 1996, 52, 14855. Other stereoselective UMCT reactions: D. P. Curran, J. Xu, Synlett 1997, 1102.