A Stereoselective Synthetic Route to (Z)-1-Arylthio Vinylstannanes

(Note: The full text of this document is currently only available in the PDF Version )

Xian Huang and Ping Zhong


Abstract

Acetylenic stannanes react with Cp2Zr(H)Cl (Cp=η5-C5H5) to give organozirconium(IV) complexes, which are trapped with arylsulfenyl chloride to afford (Z)-l-arylthio vinylstannanes.


References

  1. B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 1983, 105, 5075 CrossRef CAS.
  2. A. Alexakis and J. F. Normant, Synthesis, 1985, 72 CrossRef CAS.
  3. T.-Y. Luh and Z. J. Ni, Synthesis, 1990, 89 CrossRef CAS.
  4. J. K. Stille and J. H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138 CrossRef CAS.
  5. P. A. Magriotis, J. T. Brown and M. E. Scott, Tetrahedron Lett., 1991, 32, 5047 CrossRef CAS.
  6. P. Wipf and H. Jahn, Tetrahedron, 1996, 52, 12853 CrossRef CAS.
  7. J. W. Sung, C. W. Lee and D. Y. Oh, Tetrahedron Lett., 1995, 36, 1503 CrossRef CAS.
  8. X. Huang and L. S. Zhu, J. Chem. Soc., Perkin Trans. 1, 1996, 767 RSC.
  9. B. H. Lipshutz, R. Keil and J. C. Barton, Tetrahedron Lett., 1992, 33, 5861 CrossRef CAS.
  10. S. L. Buchwald, S. J. Lamaire, R. B. Nielsen, B. T. Watson and S. M. King, Tetrahedron Lett., 1987, 28, 3895 CrossRef CAS and references cited therein.
  11. M. W. Logue and T. Teng, J. Org. Chem., 1982, 47, 2549 CrossRef CAS.
  12. D. N. Harpp, B. T. Friedlander and R. A. Smith, Synthesis, 1979, 181 CrossRef CAS.
  13. B. T. Grobel and D. Seebach, Chem. Ber., 1977, 110, 867.
  14. T. Mukaiyama, K. Kamio, S. Kobayashi and H. Takei, Bull. Chem. Soc., 1972, 45, 3723 Search PubMed.
  15. F. M. Beringer, M. Drexler, E. M. Gindler and C. C. Lumpkin, J. Am. Chem. Soc., 1953, 75, 2705 CrossRef CAS.
  16. J. Nakayama, S. Takeue and M. Hoshino, Tetrahedron Lett., 1984, 25, 2679 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.