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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 12
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Original Articles

Improved Synthesis of Aliphatic Ketones by the Reaction of Alkylmercuric Bromides With Nickel Carbonyl in the Presence of Potassium Iodide

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Pages 1175-1179 | Published online: 06 Dec 2006

References

  • Ryang , M. and Tsutsumi , S. Synthesis , 1971 55
  • Hirota , Y. , Ryang , M. and Tsutsumi , S. 1971 . Tetrahedron Lett. , : 1531 As we have previously reported, alkylmercuric bromides react with Ni(CO)4 in DMF to give only moderate yields of aliphatic ketones, Related works using organomercurials: Condensation of α-iodomercuric ketones with aldehydes or ketones mediated by Ni(CO)4: Ryee, I., Ryu, I., Omura, H., Murai, S. and Sonoda, N., Chem. Lett., 1979, 1435: Unsymmetrical diaryl ketone synthesis: Rhee, I., Ryang, M., Watanabe, T., Omura, H., Murai, S. and Sonoda, N., Synthesis, 1977, 776
  • Treatment of alkylmercuric acetate or bromide with aqueous KI proved not to be useful for the preparation of the corresponding iodide, often bothered by decomposition of the mercurials
  • Marvel , S. C. and Gould , L. V. 1922 . J. Am. Chem. Soc. , 44 : 153 By modification of a literature method, see
  • Seyferth , D. and Spohn , J. R. 1969 . J. Am. Chem. Soc. , 90 : 540 β-Elimination is frequently encountered in the similar ketone synthesis with cobalt octacarbonyl., 1970, 91, 3037; 1970, 91, 6192.
  • Sokolov , I. V. , Bashilov , V. V. and Reutov , A. O. 1976 . J. Organometal. Chem. , 111 : C13 Oxidative addition of RHgBr to palladium complex, see
  • Ryu , I. , Matsumoto , K. , Ando , M. , Murai , S. and Sonoda , N. 1980 . Tetrahedron Lett. , 21 : 4283
  • Stetter , H. , Wasse , W. , Kahlman , H. , Landsheidt , A. and Schlender , W. 1977 . Chem. Ber. , 110 : 1007

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