Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Halogenation of Aldehydes and Ketones by Selenium (IV) Oxyhalides Generated in-situ from Selenium Dioxide and Halotrimethylsilanes

  • Published : 1995.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Bromo-and chlorotrimethylsilane react with selenium dioxide in halocarbon solvents and generate selenium oxybromide and oxychloride, respectively. These in-situ generated oxyhalides turned out to be very efficient for selective bromination and chlorination of aldehydes and ketones. Under carefully controlled reaction conditions, second and third introduction of halogens into carbonyl compounds can be greatly suppressed, and high yields of monohalo compounds were obtained. The product ratios of this halogenation reactions can be best explained if the reactions are assumed to involve intermediate β-ketoselenenyl chlorides.

Keywords

References

  1. Comprehensive Inorganic Chemistry v.2 Bagnal, K. W.;Bailar, J. C.(ed.);Emeleus, H. J.(ed.);Niholm, R.(ed.);Dickenson, A. F. T.(ed.)
  2. The Chemistry of Selenium, Tellurium and Pollonium Bagnall, K. W.
  3. Selenium Reagents and Intermediates in Organic Synthesis v.43 Claude, P.
  4. J. Org. Chem. v.53 Lee, J. G.;Kang, K. K.
  5. J. Am. Chem. Soc. v.43 Lenher, V.
  6. Aust. J. Chem. v.37 Haynes, R. K.;Indorato, C.
  7. Synthetic Reagents v.1 Pizey, J. S.
  8. J. Org. Chem. v.28 Schaefer, J. P.;Sonnenberg, F.
  9. J. Organomet. Chem. v.3 Bott, R. N.;Eaborn, C.;Rushton, B. M.
  10. Chem. Ber. v.94 Schmidbauer, H.
  11. Angew. Chem. v.70 Schmidt, M.;Schmidbauer, H.
  12. Bull. Korean. Chem. Soc. v.9 Lee, J. G.;Ha, D. S.
  13. Bull. Korean. Chem. Soc. v.8 Lee, J.G.;Ha, D. S.
  14. Bull. Korean. Chem. Soc v.8 Lee, J. G.;Ha, D. S.
  15. Acta Chem. Scand. v.411 Bisrom, A.;Wilhelmi, A. K.
  16. Chem. Zvesti v.14 Hanic, F.;Stempelova, D.
  17. Tetrahedron Lett. v.31 Lee, J. G.;Hwang, J. P.
  18. Tetrahedron Lett. v.33 Lee, J. G.;Cha, H. T.
  19. Tetrahedron Lett. v.33 Lee, J. G.;Kim, K. K.
  20. The Chemistry of α-Haloketones, α-Haloimines Kimpe, N. D.;Verhe, R.
  21. Modern Synthetic Reactions House, H. O.
  22. Am. Chem. Soc. v.70 Djerassi, C.;Scholz, C. R.
  23. Synthesis Forlani, L.
  24. Tetrahedron Lett. Armstrong, V. W.;Chishti, N. H.;Ramage, R.
  25. Synthesis Cacchi, S.;Caglioti, L.
  26. Synthesis Bongini, A.;Cainelli, G.;Contento, M.;Manescalchi, F.
  27. Synthesis Bloch, R.
  28. Tetrahedron v.29 Calo, V.;Lopez, L.;Pesce, G.;Todesco, P. E.
  29. Tetrahedron v.31 Sekiya, M.;Ito, K.;Suzuki, K.
  30. Tetrahedron v.40 Armani, E.;Dossena, R.;Marchelli, R.;Casnati, G.
  31. J. Chem. Res. (S) Bellesia, F.;Ghelfi, F.;Grndi, R.;Pagnoni, U. M.
  32. Synthetic Reagents v.5 Pizey, J. S.
  33. J. Org. Chem. v.29 Wyman, D. P.;Kaufman, R. J.
  34. J. Org. Chem. v.29 Wyman, D. P.;Kaufman, R. J.;Freeman, W. R.
  35. J. Org. Chem. v.46 Masilamani, D.;Rogic, M. M.
  36. J. Am. Chem. Soc. v.82 Corey, E. J.;Schafer, J. P.
  37. J. Am. Chem. Soc. v.98 Sharpless, K. B.;Gordon, K. M.
  38. Bull. Chem. Soc. Jpn. v.48 Uemura, S.;Onoe, A.;Okano, M.
  39. Bull. Chem. Soc. Jpn. v.50 Uemura, S.;Onoe, A.;Okano, M.
  40. J. Am. Chem. Soc. v.68 Gilliam, W. G.;Meals, R. N.;Sauer, R. D.