Reductive Cleavage of the Se–Se Bond by the Sm–Me3SiCl–H2O System: Preparation of Unsymmetrical Phenyl Selenides

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Lei Wang and Yongmin Zhang


Abstract

The reduction of diphenyl diselenide by the Sm–Me3SiCl–H2O system led to a selenide anion. This ‘living’ species reacted with organic halides, epoxides, α,β-unsaturated esters and α,β-unsaturated nitriles to afford unsymmetrical phenylselenides in good yields under mild and neutral conditions.


References

  1. The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley, Chichester, 1986, vol. 1 Search PubMed.
  2. K. B. Sharpless and R. F. Laura, J. Am. Chem. Soc., 1973, 95, 2697 CrossRef CAS.
  3. E. E. Aynsley, N. N. Greenwood and J. B. Leach, Chem. Ind., 1966, 379 Search PubMed.
  4. Y. Zhang, Y. Yu and R. Lin, Synth Commun., 1993, 23, 189 CAS.
  5. H. Suzuki, M. Yoshinaga, K. Takaoka and Y. Hiroi, Synthesis, 1985, 497 CrossRef CAS.
  6. D. Liotta, U. Sunay, H. Santiesteban and W. Markiewicz, J. Org. Chem., 1981, 46, 2605 CrossRef CAS; D. L. Klayman and W. H. H. Gunther, Organic Selenium Compounds: Their Chemistry and Biology, John Wiley, New York, 1973, p. 191 Search PubMed.
  7. F. Taboury, Bull. Soc. Chim. Fr., 1903, 29, 761.
  8. H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573 CrossRef CAS; G. A. Molander, Chem. Rev., 1992, 92, 29 CrossRef CAS; G. A. Molander, Org. React., 1994, 46, 211 CAS; G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307 CrossRef CAS.
  9. R. Yanada, N. Negoro, K. Yanada and T. Fujita, Tetrahedron Lett., 1997, 38, 3271 CrossRef CAS and references cited therein.
  10. N. Akane, Y. Kanagawa, Y. Nishiyama and Y. Ishii, Chem. Lett., 1992, 2431 CAS; N. Akane, T. Hatano, H. Kusui, Y. Nishiyama and Y. Ishii, J. Org. Chem., 1994, 59, 7902 CrossRef CAS.
  11. V. F. Patel, G. Pattenden and D. M. Thompson, J. Chem. Soc., Perkin Trans. 1, 1990, 2729 RSC.
  12. K. Haraguchi, H. Tanaka and T. Miyasaka, Tetrahedron Lett., 1990, 31, 227 CrossRef CAS.
  13. R. Raucher and G. A. Koolpe, J. Org. Chem., 1978, 43, 4252 CrossRef.
  14. G. A. Russell, P. Ngoviwatchai, H. I. Tashtoush, A. Pla-Dalmau and R. K. Khanna, J. Am. Chem. Soc., 1988, 110, 3530 CrossRef CAS.
  15. S. V. Ley, I. A. O'Neil and C. M. R. Low, Tetrahedron, 1986, 42, 5363 CrossRef CAS.
  16. P. Rollin, V. V. Bencomo and P. Sinay, Synthesis, 1984, 134 CrossRef CAS.
  17. L. A. Khazemova and V. M. Al'bitskaya, Zh. Org. Khim., 1969, 5, 1926 CAS.
  18. A. Ogawa, Y. Nishiyama, N. Kambe, S. Murai and N. Sonoda, Tetrahedron Lett., 1987, 28, 3271 CrossRef CAS.
  19. E. G. Kataev and F. G. Gabdrakhmanav, Zh. Obshch. Khim., 1967, 37, 772 CAS.
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