Rapid and mild deoxygenation of organoheteroatom oxides with the efficient electron transfer system SmI2-tetrahydrofuran-hexamethylphosphoric triamide

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 5, 1989, Pages 298-299

  Handa, Yuichi ^a   Inanaga, Junji ^a   Yamaguchi, Masaru ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049080432     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39890000298     Document Type: Article

References (16)

1. J. Drabowicz, H. Togo, M. Mikolajczyk, and S. Oae, Org. Prep. Proced. Int., 1984, 16, 171.
2. Y. Guindon, J. G. Atkinson, and H. E. Morton, J. Org. Chem., 1984, 49, 4538.
3. M. Malinowski, Synthesis, 1987, 732.
4. D. H. R. Barton, A. Fekih, and X. Lusinchi, Tetrahedron Lett., 1985, 26, 4603.
5. G. Lunn and D. B. Sansone, Synthesis, 1985, 1104.
6. N. Tokitoh and R. Okazaki, Chem. Lett., 1985, 1517 and references cited therein.
7. H. C. Brown and P. M. Weissman, J. Am. Chem. Soc., 1965, 87, 5614.
8. H. C. Brown, P. M. Weissman, and N. M. Yoon, J. Am. Chem. Soc., 1966, 88, 1458.
9. T. Imamoto, T. Takeyama, and T. Kusumoto, Chem. Lett., 1985, 1491.
10. K. L. Marsi, J. Org. Chem., 1974, 39, 265 and references cited therein.
11. B. Jousseaume, E. Chanson, and M. Pereyre, Organometallics, 1986, 5, 1271 and references cited therein.
12. 2-THF-HMPA) is highly effective for the generation of ketyls and in other electron transfer reactions. K. Otsubo, J. Inanaga, and M. Yamaguchi, Tetrahedron Lett., 1986, 27, 5763.
13. J. Inanaga, M. Ishikawa, and M. Yamaguchi, Chem. Lett., 1987, 1485.
14. K. Otsubo, K. Kawamura, J. Inanaga, and M. Yamaguchi, Chem. Lett., 1987, 1487.
15. Samarium di-iodide was introduced in organic transformations by Kagan and co-workers. P. Girard, J. L. Namy, and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693.
16. Presented at the 54th National Meeting of the Chemical Society of Japan, Tokyo, April, 1987.