View PDF Version
 
DOI: 10.1039/A906455I (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 4083-4086

Facile rhenium(IV)-mediated coupling of acetonitrile and oximes[hair space]†

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

Gabriele Wagner, Armando J. L. Pombeiro, Nadezhda A. Bokach and Vadim Yu. Kukushkin

Abstract

Addition of oximes RR′C[double bond, length half m-dash]NOH [R/R′ = Me/Me, C4H8, C5H10, C9H18, C9H16 or Me/C(Me)NOH] to the acetonitrile ligands in cis-[ReCl4(MeCN)2] proceeded smoothly at room temperature within a few minutes to give cis-[ReCl4{NH[double bond, length half m-dash] C(Me)ON[double bond, length half m-dash]CRR′}2] in almost quantitative yield. All complexes were characterized by elemental analysis, IR spectroscopy and FAB mass spectrometry. Structure determination, performed for cis-[ReCl4{NH[double bond, length half m-dash]C(Me)ON[double bond, length half m-dash] C(C5H10)}2]·MeCN and cis-[ReCl4{NH[double bond, length half m-dash]C(Me)ON[double bond, length half m-dash]C(C9H18)}2], show that the cis geometry of the starting complex is conserved in the products.

References

  1. V. Yu. Kukushkin, D. Tudela and A. J. L. Pombeiro, Coord. Chem. Rev., 1996, 156, 333 CrossRef CAS.
  2. V. Yu. Kukushkin and A. J. L. Pombeiro, Coord. Chem. Rev., 1999, 181, 147 CrossRef CAS.
  3. K. Maeda, T. Hosokawa, S.-I. Murahashi and I. Moritani, Tetrahedron Lett., 1973, 5075 CrossRef CAS.
  4. T. Hosokawa, N. Shimo, K. Maeda, A. Sonoda and S.-I. Murahashi, Tetrahedron Lett., 1976, 383 CrossRef CAS.
  5. R. Baker and M. S. Nobbs, Tetrahedron Lett., 1977, 3759 CrossRef CAS.
  6. A. T. Hutton, D. M. McEwan, B. L. Shaw and S. W. Wilkinson, J. Chem. Soc., Dalton Trans., 1983, 2011 RSC.
  7. L. Caglioti, B. Galli, F. Gasparrini and G. Natile, in Congresso Interdivisionale della Societa Chimica Italiana, San Benedetto del Tronto, Atti, 1990, p. 521 Search PubMed.
  8. J. Grigg, D. Collison, C. D. Garner, M. Helliwell, P. A. Tasker and J. M. Thorpe, J. Chem. Soc., Chem. Commun., 1993, 1807 RSC.
  9. V. Zerbib, F. Robert and P. Gouzerh, J. Chem. Soc., Chem. Commun., 1994, 2179 RSC.
  10. V. Yu. Kukushkin, V. K. Belsky and D. Tudela, Inorg. Chem., 1996, 35, 510 CrossRef CAS.
  11. V. Yu. Kukushkin, D. Tudela, Yu. A. Izotova, V. K. Belsky and A. I. Stash, Inorg. Chem., 1996, 35, 4926 CrossRef CAS.
  12. V. Yu. Kukushkin, V. K. Belsky, E. A. Aleksandrova, V. E. Konovalov and G. A. Kirakosyan, Inorg. Chem., 1992, 31, 3836 CrossRef CAS.
  13. V. Yu. Kukushkin, T. B. Pakhomova, Yu. N. Kukushkin, R. Herrmann, G. Wagner and A. J. L. Pombeiro, Inorg. Chem., 1998, 37, 6511 CrossRef CAS.
  14. G. Wagner, A. J. L. Pombeiro, Yu. N. Kukushkin, T. B. Pakhomova, A. D. Ryabov and V. Yu. Kukushkin, Inorg. Chim. Acta, 1999, 292, 272 CrossRef CAS.
  15. V. Yu. Kukushkin, T. B. Pakhomova, N. A. Bokach, G. Wagner, M. L. Kuznetsov, M. Galanski and A. J. L. Pombeiro, Inorg. Chem., in press Search PubMed.
  16. V. Yu. Kukushkin, I. V. Ilichev, G. Wagner, J. J. R. Fraústo da Silva and A. J. L. Pombeiro, J. Chem. Soc., Dalton Trans., 1999, 3047 RSC.
  17. A. J. L. Pombeiro, D. L. Hughes and R. L. Richards, J. Chem. Soc., Chem. Commun., 1988, 1052 RSC.
  18. J. J. R. Fraústo da Silva, M. F. C. Guedes da Silva, R. A. Henderson, A. J. L. Pombeiro and R. L. Richards, J. Organomet. Chem., 1993, 461, 141 CrossRef CAS.
  19. G. Rouschias and G. Wilkinson, J. Chem. Soc. A, 1968, 489 RSC.
  20. D. A. Edwards and J. Marshalsea, Synth. React. Inorg. Metal-Org. Chem., 1974, 4, 573 Search PubMed.
  21. A. D. Hamer and R. A. Walton, Synth. React. Inorg. Metal-Org. Chem., 1975, 5, 139 Search PubMed.
  22. R. E. Myers and R. A. Walton, Inorg. Chem., 1976, 15, 3065 CrossRef CAS.
  23. R. E. Myers, Diss. Abstr. Int. B, 1978, 39, 737 Search PubMed.
  24. A. G. Kolchinskii and N. V. Ulko, Ukr. Khim. Zh., 1981, 47, 159 Search PubMed.
  25. C. Pearson and A. L. Beauchamp, Inorg. Chem., 1998, 37, 1242 CrossRef CAS.
  26. L. J. Bellamy, The Infrared Spectra of Complex Molecules, 2nd edn., Methuen, London, 1996 Search PubMed.
  27. N. B. Colthup, L. H. Daly and S. E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York, 1964 Search PubMed.
  28. A. L. Spek, Acta Crystallogr., Sect. A, 1990, 46, C34.
  29. C. Pearson and A. L. Beauchamp, Inorg. Chim. Acta, 1995, 237, 13 CrossRef CAS.
  30. V. Yu. Kukushkin, Zh. Neorg. Khim., 1988, 33, 1905 Search PubMed; Russ. J. Inorg. Chem. (Engl. Transl.), 1988, 33, 1085 Search PubMed.
  31. M. F. C. Guedes da Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, C. Amatore and J.-N. Verpeaux, Organometallics, 1994, 13, 3943 CrossRef CAS.
  32. M. F. C. Guedes da Silva, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, C. Amatore and J.-N. Verpeaux, Inorg. Chem., 1998, 37, 2344 CrossRef.
  33. H. Seino, Y. Tanabe, Y. Ishii and M. Hidai, Inorg. Chim. Acta, 1998, 280, 163 CrossRef CAS.
  34. R. E. Kitson and N. E. Grith, Anal. Chem., 1952, 24, 334 CrossRef CAS.
  35. E. Beckmann, Liebigs Ann. Chem., 1888, 250, 322 Search PubMed.
  36. V. A. Strel'tsov and V. E. Zavodnik, Kristallografia, 1989, 34, 1369 Search PubMed.
  37. G. M. Sheldrick, SHELXTL User Manual, Revision 3, Nicolet XRD Corp., Madison, WI, 1981 Search PubMed.
  38. G. M. Sheldrick, SHELX-97, University of Göttingen, 1997.
  39. L. G. Axelrud, Yu. N. Grin, P. Yu. Zavalii, V. K. Pecharsky and V. S. Fundamensky, CSD universal program package for single crystal and/or powder structure data treatment Collected Abstracts, XIIth European Crystallographic Meeting, Moscow, August 1989; USSR Academy of Sciences, Moscow, 1989, p. 155 Search PubMed.
  40. International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1974, vol. IV Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.