Two types of intramolecular homolytic substitution reactions at group XIV atoms: Unusual radical 1,4-Sn shifts from Si to C and carbonylative SHi reaction at Si

Chemical Communications

Volumn 3, Issue 10, 2003, Pages 1190-1191

  Studer, Armido ^a   Amrein, Stephan ^a   Matsubara, Hiroshi ^b   Schiesser, Carl H ^b   Doi, Takashi ^c   Kawamura, Tomonori ^c   Fukuyama, Takahide ^c   Ryu, Ilhyong ^c  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (STANNYLPROPYL)SILYL DERIVATIVE; 3 (STANNYLSILYL)PROPYL DERIVATIVE; 4 [(TRIMETHYLSTANNYL)DIPHENYLSILYL]BUTANOYL DERIVATIVE; CARBON; CARBON MONOXIDE; RADICAL; SILICON; TIN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; ATOM; CALCULATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS;

EID: 0038824023     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b301755a     Document Type: Article

References (36)

1. Radicals in Organic Synthesis, ed. P. Renaud and M. P. Sibi, vols 1 and 2, Wiley-VCH, Weinheim, Germany, 2001
2. C. H. Schiesser, L. M. Wild: Tetrahedron, 1996, 52, 13265
3. J. C. Walton: Acc. Chem. Res., 1998, 31, 99
4. A. L. J. Beckwith: J. Chem. Soc. Rev., 1993, 22, 143
5. N. Al-Maharik, L. Engman, J. Malmström, C. H. Schiesser: J. Org. Chem., 2001, 66, 6286
6. M. W. Carland, R. L. Martin, C. H. Schiesser: Tetrahedron Lett., 2001, 42, 4737
7. C. L. Winn, J. M. Doodman: Tetrahedron Lett., 2001, 42, 7091
8. R. Leardini, H. McNab, M. Minozzi, D. Nanni: J. Chem. Soc., Perkin Trans. 1, 2001, 1072
9. T. Ooi, M. Furuya, D. Sakai, Y. Hokke, K. Maruoka: Synlett, 2001, 541
10. Y. Nishiyama, Y. Hada, M. Anjiki, K. Miyake, S. Hanita, N. Sonoda: J. Org. Chem., 2002, 67, 1520
11. I. Ryu, T. Okuda, K. Nagahara, N. Kambe, M. Komatsu, N. Sonoda: J. Org. Chem., 1997, 62, 7550
12. C. Chatgilialoglu, D. Crich, M. Komatsu, I. Ryu: Chem. Rev., 1999, 99, 1991
13. I. Ryu, N. Sonoda: Angew. Chem., Int. Ed. Engl., 1996, 35, 1050
14. I. Ryu, N. Sonoda, D. P. Curran: Chem. Rev., 1996, 96, 177
15. A. Studer: Angew. Chem., Int. Ed., 1998, 37, 462
16. A. Studer, H. Steen: Chem. Eur. J., 1999, 5, 759
17. S. Amrein, M. Bossart, T. Vasella, A. Studer: J. Org. Chem., 2000, 65, 4281
18. A. Studer, M. Bossart, T. Vasella: Org. Lett., 2000, 2, 985
19. C. H. Schiesser, M. L. Styles, L. M. Wild: J. Chem. Soc., Perkin Trans. 2, 1996, 2257
20. J. A. Soderquist, A. Hassner: J. Org. Chem., 1980, 45, 541
21. A. Hassner, J. A. Soderquist: Tetrahedron Lett., 1980, 21, 429
22. D. Dakternieks, D. J. Henry, C. H. Schiesser: Organometallics, 1998, 17, 1079
23. S.-Y. Chang, Y.-F. Shao, S.-F. Chu, G.-T. Fan, Y.-M. Tsai: Org. Lett., 1999, 1, 945
24. S. Kim, S. Lee, J. S. Koh: J. Am. Chem. Soc., 1991, 113, 5106
25. S. Kim, J. S. Koh: Chem. Commun., 1992, 1377
26. E. Hasegawa, K. Ishiyama, T. Kato, T. Horaguchi, T. Shimizu, S. Tanaka, Y. Yamashita: J. Org. Chem., 1992, 57, 5352
27. S. Kim, K. M. Yeon, K. S. Yoon: Tetrahedron Lett., 1997, 38, 3919
28. S. Kim, M. S. Jung, C. H. Cho, C. H. Schiesser: Tetrahedron Lett., 2001, 42, 943
29. H. Sano, D. Asanuma, M. Kosugi: Chem. Commun., 1999, 1559
30. S. Kim, K. M. Lim: Chem. Commun., 1993, 1152
31. C. Chatgilialoglu, K. U. Ingold, J. C. Scaiano: J. Am. Chem. Soc., 1981, 103, 7739
32. C. H. Schiesser, L. M. Wild: J. Org. Chem., 1998, 63, 670
33. C. H. Schiesser, L. M. Wild: J. Org. Chem., 1999, 64, 1131
34. S. M. Horvat, C. H. Schiesser, L. M. Wild: Organometallics, 2000, 19, 1239
35. S. Kim, S. M. Horvat, C. H. Schiesser: Aust. J. Chem., 2002, 55, 753
36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, Revision A.7, Gaussian Inc., Pittsburgh, PA, 1998