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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, E-mail: taberdfudel.edu

D. F. Taber, C. G. Nelson, J. Org. Chem., 2006, 71, 8973-8974.

DOI: 10.1021/jo061420v (free Supporting Information)


Abstract

The 1:1 homogenate of potassium hydride with paraffin [KH(P)] is solid, convenient to use, and stable at room temperature. On suspension in THF with phosphonium salts, KH(P) rapidly generates ylides for Wittig condensations with aromatic, aliphatic, and α,β-unsaturated aldehydes with high Z selectivity.

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Key Words

Wittig reaction


ID: J42-Y2006-3760