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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 9
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Original Articles

Isolation and Reactions of the Lithium Di-enolate of Diethyl Succinate

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Pages 687-696 | Published online: 06 Dec 2006

References

  • Johnson , W. H. and Dauben , G. H. 1951 . Org. Reactions , 6 : 1 For a recent review see
  • Kofron , W. G. and Wideman , L. G. 1972 . J. Org. Chem. , 37 : 555 A number of synthetic equivalents of 1, each possessing carbonyl functionality less reactive than ester, such as carboxylate2a, imide anion2b, and amide anion2c, have been reported
  • Bryant , D. R. and Hauser , C. R. 1961 . J. Am. Chem. Soc. , 83 : 3468
  • Adams , T. and Hauser , C. R. 1977 . J. Org. Chem. , 42 : 3029
  • Garratt , P. J. and Zahler , R. 1978 . J. Am. Chem. Soc. , 100 : 7753 Garratt has quenched the enolates produced by reaction of cyclobutane-1,2-dicarboxylates with two equivalents of LDA with a variety of carbon acids and concluded that 1,2-diester dianions may be much more readily prepared than is generally assumed
  • Reutrakul , V. , Kusamran , K. and Wattanasin , S. 1977 . Heterocycles , 6 : 715
  • Rathke , M. W. and Lindert , A. 1971 . J. Am. Chem. Soc. , 93 : 2318
  • Jung , M. and Shaw , T. 1977 . Tetrahedron Lett. , : 3305 Oxime anions are kinetically deprotonated syn to the oxygen atom. Jung has suggested that base coordinates with the oxime metal-oxygen bond to facilitate syn deprotonation:. A similar coordinator of LDA to mono-enolate would account for preferential formation of 2
  • 1943 . Vol. 2 , 264 Organic Synthesis Coll.

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