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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 5
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Original Articles

The Preparation of New C(α)-Dianions

, &
Pages 339-347 | Received 10 Mar 1976, Published online: 06 Dec 2006

References

  • To whom inquires should be addressed.
  • Hauser , C. R. and Harris , T. M. 1958 . J. Am. Chem. Soc. , 80 : 6360
  • Light , R. J. and Hauser , C. R. 1961 . J. Org. Chem. , 26 : 1716
  • Wolfe , J. F. , Harris , T. M. and Hauser , C. R. 1964 . ibid. , 29 : 3249
  • O'Sullivan , W. I. , Swamer , F. W. , Humphlett , W. J. and Hauser , C. R. 1961 . ibid. , 26 : 2306
  • Puterbaugh , W. H. and Hauser , C. R. 1963 . ibid. , 28 : 3465
  • Harris , T. M. and Harris , C. M. 1969 . “ 2 ” . In Org. Reactions Vol. 17 , New York : John Wiley and Sons, Inc. . Chapt
  • Beam , C. F. , Bissell , R. L. and Hauser , C. R. 1970 . J. Org. Chem. , 35 : 2083
  • Henoch , F. E. , Hampton , K. G. and Hauser , C. R. 1969 . J. Am. Chem. Soc. , 91 : 676
  • Beam , C. F. , Dyer , M. C. D. , Schwarz , R. A. and Hauser , C. R. 1970 . J. Org. Chem. , 35 : 1806
  • Beam , C. F. , Park , C. A. , Sandifer , R. M. and Kaiser , E. M. 1975 . Southeast-Southwest, Amer. Chem. Soc. Region. Meetg., Memphis, TN , October, paper 399
  • Beam , C. F. , Foote , R. S. and Hauser , C. R. 1972 . J. Heterocycl. Chem. , 9 : 183
  • Griffiths , J. S. , Beam , C. F. and Hauser , C. R. 1971 . J. Chem. Soc., C, C , : 974
  • Foote , R. S. , Beam , C. F. and Hauser , C. R. 1970 . J. Heterocycl. Chem. , 7 : 589
  • Reames , D. C. , Harris , C. E. , Dasher , L. W. , Sandifer , R. M. , Hollinger , W. M. and Beam , C. F. 1975 . J. Heterocycl. Chem. , 12 : 779
  • Beam , C. F. , Reames , D. C. , Harris , C. E. , Dasher , L. W. , Hollinger , W. M. , Shealy , N. L. , Sandifer , R. M. , Perkins , M. and Hauser , C. R. 1975 . J. Org. Chem. , 40 : 514
  • Beam , C. F. , Sandifer , R. M. , Foote , R. S. and Hauser , C. R. 1976 . Synth. Comm. , 6 : 5
  • Beam , C. F. , Foote , R. S. and Hauser , C. R. 1971 . J. Chem. Soc., C , : 1658
  • Sandifer , R. M. , Dasher , L. W. , Hollinger , W. M. , Wayne Thomas , C. , Reames , D. C. , Beam , C. F. , Foote , R. S. and Hauser , C. R. 1975 . J. Heterocycl. Chem. , 12 : 1159
  • In many cases, the initial evidence for the formation of a multiple anion was the orange to red-black color of the solution obtained after the addition of n-butyllithium was complete. See also the mechanism discussion in reference 16
  • Hauser prepared the dianions at -78[ddot] and most of our dianions were prepared at 0[ddot]. Some in-between temperatures, or C(α)-DIANONS sequential addition of two different bases may be necessary to prepare and condense these dianions with aldehydes. See also: reference 9
  • The Aldol-type condensation and the retro-Aldol cleavage appears to be time dependent, and optimum condensation times may vary from a few seconds to more than 30 min. See also: reference 3

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