Reaction of diisobutylaluminium hydride with selenium and tellurium: New reagents for the synthesis of seleno- and telluro-amides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1998, Pages 647-650

  Li, Guang Ming ^a   Zingaro, Ralph A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748636292     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a707792k     Document Type: Article

References (26)

1. For some recent reviews: (a) A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. E. Winterfeldt, Pergamon, Oxford, UK, 1991, vol. 6, pp. 461-484;
2. (b) C. P. Dell, in Comprehensive Organic Functional Group Transformations, ed. C. J. Moody, Pergamon, Oxford, UK, 1995, vol. 5, pp. 565-628.
3. (a) K. A. Lerstrup and L. Henriksen, J. Chem. Soc., Chem. Commun., 1979, 1102;
4. (b) M. Segi, A. Kojima, T. Nakajima and S. Suga, Synlett, 1991, 2, 105;
5. (c) G. M. Li, R. A. Zingaro, M. Segi, J. H. Reibenspies and T. Nakajima, Organometallics, 1997, 16, 756.
6. G. M. Li, J. H. Reibenspies and R. A. Zingaro, Heteroatom Chem., in the press.
7. Some selected monographs and review articles: (a) Selenium Reagents and Intermediates in Organic Synthesis, ed. J. E. Baldwin, Pergamon, Oxford, UK, 1986;
8. (b) The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1986, vol. 1;
9. (c) The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai, Wiley, New York, 1987, vol. 2;
10. (d) K. J. Irgolic, in Houben-Weyl-Methoden der Organischen Chemie, ed. D. Klayman, 4th edn., Georg Thieme, Stuttgart, 1990, vol. E12b;
11. (e) N. Petragnani, in Tellurium in Organic Synthesis, Academic Press, New York, 1994;
12. (f) A. Krief, in Comprehensive Organometallic Chemistry II, ed. A. McKillop, Pergamon, Oxford, UK, 1995, vol. 11, ch. 13, pp. 515-569;
13. (g) N. Petragnani, in ref. 4f, chapter 14, pp. 571-601;
14. (h) F. S. Guziec, Jr. and L. J. Guziec, in Comprehensive Organic Functional Group Transformations, ed. G. Pattenden, Pergamon, Oxford, UK, 1995, vol. 3, pp. 381-401.
15. (a) M. Segi, T. Koyama, Y. Takata, T. Nakajima and S. Suga, J. Am. Chem. Soc., 1989, 111, 8749;
16. (b) M. Segi, T. Koyama, T. Nakajima, S. Suga, S. Murai and N. Sonoda, Tetrahedron Lett., 1989, 30, 2095;
17. (c) G. M. Li, M. Segi and T. Nakajima, Tetrahedron Lett., 1992, 33, 3515;
18. (d) M. Segi, T. Takahashi, H. Ichinose, G. M. Li and T. Nakajima, Tetrahedron Lett., 1992, 33, 7865;
19. (e) G. M. Li, T. Kamogawa, M. Segi and T. Nakajima, Chem. Express, 1993, 8, 53.
20. A part of this work has been presented at the 7th International Conference on the Chemistry of Selenium and Tellurium (ICCST-7), July 1997, Vaalsbroek Castle, The Netherlands.
21. 2 (E: Se, Te) increased up to 20%.
22. 13C) measurement has proved that DIBAL-H is stable under these conditions.
23. 8toluene-THF solution), see: M. Segi and T. Nakajima, Yuki Gosei Kagaku Kyokai Shi, 1995, 53, 678.
24. (a) M. Lardon, J. Am. Chem. Soc., 1970, 92, 5063;
25. (b) P. Granger, S. Chapelle, W. McWhinnie and A. Al-Rubaie, J. Organomet. Chem., 1981, 220, 149.
26. 2 to elute selenoamides or telluroamides. For compounds 3 and 13, acetone was used as the final solvent.