Reaction of 1,3-diselenanes with organolithiums

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 8011-8014

  Krief, Alain ^a   Defrère, Laurent ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030605110     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01812-6     Document Type: Article

References (18)

1. 1. Krief, A.; Defrère, L. Tetrahedron Lett. 1996, 37, 2667.
2. 2. (a) Krief, A. in "Comprehensive Organic Synthesis" Trost, B. M.; Fleming, I. Ed.; Pergamon Press: Oxford, 1991, Vol. 3, pp 629
3. (b) Krief, A. in "The Chemistry of Organic Selenium and Tellurium Compounds" Patai, S. Ed., John Wiley and Sons, Chichester 1987, 2, 675
4. (c) Reich, H. J. in "Organoselenium Chemistry" Liotta, D. Ed., John Wiley, Chichester 1987, 243
5. (d) Krief, A. Tetrahedron 1980, 36, 2531.
6. 3. Krief, A.; Dumont, W.; Clarembeau, M.; Bernard, G.; Badaoui, E. Tetrahedron, 1989, 45, 2005.
7. 4. The cleavage by BuLi of the C-Se bond of diselenanes derived from ketones has been already described : (a) Krief, A.; Badaoui, E.; Dumont, W. Tetrahedron Lett. 1993, 34, 8517
8. (b) Reich, HJ.; Bowe, M.D. J. Am. Chem. Soc. 1990, 112, 8994.
9. 5. These results will be disclosed in the full paper.
10. 6. For related results on 1,3-dithianes : (a) Hartmann, A. A.; Eliel, E. L J. Am. Chem. Soc. 1971, 93, 2572
11. (b) Eliel, E. L.; Abatjoglou, A. G.; Hartmann, A. A. J. Am. Chem. Soc. 1972, 94, 4786
12. (c) Eliel, E. L.; Hartmann, A. A.; Abatjoglou, A. G. J. Am. Chem. Soc. 1974, 96, 1807
13. (d) Eliel, E. L. Tetrahedron 1974, 30, 1503
14. (e) Abatjoglou, A. G.; Eliel, E. L.; Kuyper, L. F. J. Am. Chem. Soc. 1977, 99, 8262
15. (f) Jernigan, M. T.; Eliel, E. L. J. Am. Chem. Soc. 1995, 117, 9638.
16. 7. The authors thank Prof. T. Cohen for a valuable discussion on that matter during his visit to Namur.
17. 8. We have previously described that related 2-phenyl-1,3-dithianes possess also a very high propensity to be cleaved by n-BuLi and therefore that this reagent prefers to react on the sulfur atom rather than on the hydrogen attached on C-2, as it is usually the case, with others 1,3-dithianes : Krief, A.; Kenda, B.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 2509.
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