Potassium Hydride in Paraffin:  A Useful Base for Organic Synthesis

Douglass F. Taber* and Christopher G. Nelson
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716 taberdf@udel.edu
J. Org. Chem., 2006, 71 (23), pp 8973–8974
DOI: 10.1021/jo061420v
Publication Date (Web): October 10, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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The preparation of potassium hydride as a 1:1 homogenate with paraffin, termed KH(P), is reported. KH(P), a solid at room temperature, is stable without special handling. On suspension in THF with a phosphonium salt, KH(P) rapidly generates the ylide. Wittig condensation with aromatic, aliphatic, and α,β-unsaturated aldehydes proceeds with high Z selectivity. KH(P) should be a generally useful base for organic synthesis.

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History

  • Published In Issue November 10, 2006
  • Received July 7, 2006

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