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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 1
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Original Articles

Trimethylsilylmethyl Ketones in Synthesis A Regiospecific Synthesis of β, γ-Unsaturated Esters, Amides and Nitriles

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Pages 15-19 | Received 13 Sep 1974, Published online: 05 Dec 2006

References

  • Whitmore , F. C. , Sommer , L. H. , Gold , J. and Van Strien , R. E. 1947 . J. Amer. Chem. Soc. , 69 : 1151
  • Hauser , C. R. and Hance , C. R. 1952 . J. Amer. Chem. Soc. , 74 : 5091
  • Hudrlik , P. F. and Peterson , D. 1974 . Tetrahedon Lett. , : 1133
  • Jorgenson , M. 1970 . Org. React. , 18 : 1
  • Addition of 2 moles of butyllithium to trimethylsilyl acetic acid gave none of desired product
  • (CH3)3SiCH2CO2H Presumably, enolization competes effectively with addition
  • Rathke , M. W. and Sullivan , D. F. 1973 . J. Amer. Chem. Soc. , 95 : 3050
  • Seebach , D. and Crouse , D. N. 1968 . Chem. Ber. , 101 : 3113
  • Kaiser , E. M. and Hauser , C. R. 1968 . J. Org. Chem. , 33 : 3402
  • Perchloric acid in CCl4 was used for the elimination of trimethylsilanol
  • For hindered ketones such as 2 we observed ca. 20% enolization. Hence, the yield given represents an additional recycling of the initial reaction product
  • Acknowledgment is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society for support of this research

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