Synthetic utility of 1,1,2,2-tetraaryIdisilanes: Radical reduction of alkyl phenyl chalcogenides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1999, Pages 2891-2896

  Yamazaki, Osamu ^a,b   Togo, Hidco ^b   Yokoyama, Masataka ^a  

^a Graduate School of Science and Technology   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002344233     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905937g     Document Type: Article

References (37)

1. B. Giese, Radicals in Organic Synthesis: Formation of CarbonCarbon Bonds, ed.J. E. Baldwin, Pergamon Press, Oxford, 1986;
2. J. Fossey, D. Lefort and J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995.
3. C. Chatgilialoglu, K.U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1982, 104, 5123;
4. J. Lusztyk, B. Maillard and K. U Ingold, J. Org. Chem., 1986, 51, 2457;
5. B. Giese, B. Kopping and C. Chatgilialoglu, Tetrahedron Lett., 1989, 30, 681;
6. B. Giese and K.J. Kulicke, Synlett, 1990, 91;
7. D. H. R. Barton, D. O. Jang and J. Cs. Jaszberenyi, Tetrahedron Lett., 1990, 31,4681;
8. A. Albert! and C. Chatgilialoglu, Tetrahedron, 1990, 46, 3963;
9. S.J. Cole, J. N. Kirwan, B. P. Roberts and C. R. Willis, J. Chem. Soc., Perkin Trans. 1, 1991, 103;
10. D.H. R. Barton, D. O. Jang and J. Cs. Jaszberenyi, Synlett, 1991, 435;
11. D.H. R. Barton, D. O. Jang and J. Cs. Jaszberenyi, Tetrahedron Lett., 1991, 32, 2569;
12. D.H. R. Barton, D. O. Jang and J. Cs. Jaszberenyi, Tetrahedron Let., 1991, 32, 7187;
13. C. Chatgilialoglu, Ace. Chem. Res., 1992, 25, 188; C. Chatgilialoglu, Chem. Rev., 1995, 95, 1229;
14. M.B. Haque and B. P. Roberts, Tetrahedron Lett., 1996,37,9123.
15. M. Ballestri, C. Chatgilialoglu, K.B. Clark, D. Griller, B. Giese and B. Kopping, J. Org. Chem., 1991,56, 678.
16. D.H. R. Barton, D. O. Jang and J. Cs. Jaszberenyi, Tetrahedron, 1993,49,7193.
17. O. Yamazaki, H. Togo, G. Nogami and M. Yokoyama, Bull. Chem. Soc,Jpn., 1997,70,2519.
18. O. Yamazaki, H. Togo, S. Matsubayashi and M. Yokoyama, Tetrahedron Lett., 1998, 39, 1921; O. Yamazaki, H. Togo, S. Matsubayashi and M. Yokoyama, Tetrahedron, 1999,55, 3735.
19. A mixture of 1-deoxy derivative (A) and 2-deoxy derivative (B) was obtained as reduction products. The ratios of A and B were determined to be 92:8 (EtjB) and 72:28 (AIBN) from 'H NMR spectra, respectively.
20. H.-G. Korth, R. Sustmann, K.S. Gröninger, M. Leisung and B. Giese, J. Org. Chem., 1988,53,4364.
21. Direct reduction product (C) and JV-deprotected reduction product (D) was obtained. The ratios of C and D were 95:5 (Et3B) and 82:18 (AIBN), respectively.
22. T. Nakano, H. Nakamura and Y. Nagai, Chem. Lett., 1989, 83.
23. D.L. J. Clive, G. J. Chittattu, V. Farina, W. A. Kiel, S. M. München, C. G. Russell, A. Singh, C. K. Wong and N. J. Curtis, J. Am. Chem. . Soc., 1980,102,4438.
24. T.G. Back, V. I. Birss, M. Edwards and M. V. Krishna, J. Org. Chem., 1988,53,3815.
25. T.G. Back, D. L. Baron and K. Yang, J. Org. Chem., 1993,58,2407.
26. M. Sakakibara, K. Katsumata, Y. Watahabe, T. Toru and Y. Ueno, Synthesis, 1992, 377.
27. M.A. Lucas and C. H. Schiesser, J. Org. Chem., 1996, 61, 5754.
28. A. Mallet, J.-M. Mallet and P. Sinay, Tetrahedron: Asymmetry, 1994, 5,2593.
29. H. Togo, T. Muraki and M. Yokoyama, Synthesis, 1995, 155.
30. W. He, H. Togo, Y. Waki and M. Yokoyama, J. Chem. Soc., Perkin Trans. 1,1998,2425.
31. P.J. Garegg and B. Samuelsson, J. Client. Soc., Perkin Trans, l, 19SO, 2866.
32. J.A. Bennek and G. R. Gray, J. Org. Cltcm., 1987,52, 892.
33. P. Heath, J. Mann, B. Walsh and A. H. Wadsworth, J. Chein. Soc., Perkin Trans, l, 1983,2675.
34. M. Sato, Nippon Kcigaku Kaislii, 1997, 508.
35. K. Tatsuta, K. Fujimoto, M. Kinoshita and S. Umezawa, Carbohydr. Res., 1997, 54, 85.
36. M. Michalska and J. Borowiecka, J. Carbohydr. Chem., 1983,2,99.
37. M. Oba and K. Nishiyama, Tetrahedron, 1994,50, 10193.