A Convenient in Situ Preparation of Trikethylsilyl Iodide

Synthetic Communications

Volumn 9, Issue 10, 1979, Pages 931-939

  Seitz, David E ^a   Ferreira, Lawrence ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345266911     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397917908064215     Document Type: Article

References (34)

1. M. E. Jung and M. A. Lyster, J. Org. Chem., 42, 3761 (1977)
2. J. Minamikawa and A. Brossi, Tetrahedron Lett., 3085 (1978)
3. B. I. Rosen and W. P. Weber, J. Org. Chem., 42, 3463 (1977)
4. M. G. Voronkov, E. I. Dubinskaya, V. G. Komarov and S. F. Pavlov, Zh, Obshch. Khim., 46, 1908 (1976)
5. M. G. Voronkov, V. E. Puzanova, S. F. Pavlov and E. I. Dubinskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 448 (1975).
6. M. E. Jung and M. A. Lyster, J. Am. Chem. Soc., 99, 968 (1977)
7. T.-L. Ho and G. A. Olah, Angew. Chem., 88, 847 (1976).
8. G. M. Blackburn and D. Ingleson, J. Chem. Soc., Chem. Commun., 870 (1978).
9. M. E. Jung and M. A. Lyster, J. Chem. Soc., Chem. Commun., 315 (1978).
10. M. E. Jung, W. A. Andrus and P. L. Ornstein, Tetrahedron Lett., 4175 (1977).
11. G. A. Olah, B. G. B. Gupta and S. C. Narang, Synthesis, 583 (1977)
12. K. C. Nicolaou, W. E. Barnette and R. L. Magolda, J. Am. Chem. Soc., 100. 2567 (1978)
13. M. E. Jung, M. A. Mazurek and R. M. Lim, Synthesis, 588 (1978).
14. M. E. Jung and P. L. Ornstein, Tetrahedron Lett., 2659 (1977).
15. T.-L. Ho, Synthetic Commun., 2, 233 (1979).
16. M. E. Jung, A. B. Mossman and M. A. Lyster, J. Org. Ghem., 43, 3698 (1978).
17. For the preparation of 1 from trimethylsilyl chloride, see M. E. Jung, reference 1. Trimethylsilyl iodide is also commercially available from several suppliers.
18. T.-L. Ho and G. A. Olah, Synthesis, 417 (1977)
19. T.-L. Ho and G. A. Olah, Proc. Natl. Acad. Sci. USA, 75, 4 (1978).
20. B. O. Pray, L. H. Sommer, G. M. Goldberg, G. T. Kerr, P. A. DiGiorgio and F. C. Whitmore, J. Am. Chem. Soc., 20, 433 (1948).
21. M. E. Jung and T. A. Blumenkopf, Tetrahedron Lett., 3657 (1978).
22. D. R. Weyenberg and L. H. Toporcer, J. Am. Chem. Soc., 84, 2843 (1960).
23. T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 2523 (1978)
24. T. Morita, Y. Okamoto and H. Sakurai, J, Chem. Soc., Chem. Commun., 874 (1978)
25. Y. Machida, S. Nomoto and I. Saito, Synthetic Commun., 2, 97 (1979)
26. A. H, Schmidt and M. Russ, Chem.-Ztg., 102, 2665 (1978)
27. G. A. Olah, S. C. Narang, B. G. B. Gupta and R. Malhotra, Synthesis, 61 (1979)
28. G. A. Olah, S. C, Narang, B. G. B. Gupta and R. Malhotra, J. Org. Chem., 44, 1247 (1979)
29. D. E. Seitz and L. Ferreira, Synthetic Commun., 9, 451 (1979).
30. S. J. Band and I. M. T. Davidson, Trans. Farad. Soc., 66, 406 (1970).
31. For a brief description of the solution reaction of 5 and iodine, see: Chem. Abstr., 49, 11542 (1955)
32. J. N. LePage, W. Lindner, G. Davies, D. E. Seitz and B. L. Karger, Anal. Chem. 51,, 433 (1979)
33. J.N. Le-Page, W. Lindner, G. Davies, D. E. Seitz and B. L. Karger, J. Chromatogr., submitted.
34. Atlas of Spectral Data and Physical Constants for Organic Compounds”, vol.3, p. 700, CRC Press. 1975.