Practical synthesis of (R,R)- and (S,S)-Bis[2,6-bis(1-ethoxyethyl)phenyl] diselenide

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1875-1876

  Déziel, Robert ^a   Malenfant, Eric ^a   Bélanger, Guillaume ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042953966     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951919h     Document Type: Article

References (9)

1. Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bemier, J. J. Org. Chem. 1993, 58, 3619.
2. (b) Déziel, R.; Malenfant, E. J. Org. Chem. 1995, 60, 4660.
3. Protocol based on a similar transformation: McKinnon, D. M.; Wong, J. Y. Can. J. Chem. 1971, 49, 2018.
4. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861. Corey, E. J.; Link. J. O. Tetrahedron Lett. 1992, 33, 4141 and references cited therein.
5. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861. Corey, E. J.; Link. J. O. Tetrahedron Lett. 1992, 33, 4141 and references cited therein.
6. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861. Corey, E. J.; Link. J. O. Tetrahedron Lett. 1992, 33, 4141 and references cited therein.
7. Purchased from Aldrich Chemial Co Inc. For a good review on this reagent see: Dhar, R. K. Aldrichim. Acta 1994, 27, 43.
8. We also obtained some of the R,S (meso) isomer (6.5%) which was easily separated by column chromatography on silica gel.
9. Prepared according to: Coulson, E. A. J Chem. Soc 1937, 1298.