Allylpotassium is an organopotassium compound with the molecular formula CH2=CHCH2K. It is a colorless, extremely air-sensitive compound that is usually generated and handled in solution. It is synthesized by metalation of propylene with Schlosser's base, a mixture of potassium tert-butoxide and butyl lithium:

CH2=CHCH3 + LiC4H9 + KOC(CH3)3 → KCH2CHCH2 + C4H10 + LiOC(CH3)3

Consistent with its extreme air-sensitivity, allylpotassium is highly nucleophilic. For example, it adds to pyridine, allowing the synthesis of 4-allyl-1,4-dihydropyridines. Trimethylsilyl-substituted allylpotassium have been characterized by X-ray crystallography

Further reading

  • Giner, J. L., Margot, C., & Djerassi,C (April 1989). . The Journal of Organic Chemistry. 54 (9): 2117–2125. doi:.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  • Thompson, T. B., & Ford, W. T. (September 1979). . Journal of the American Chemical Society. 101 (19): 5459–5464. Bibcode:. doi:.{{cite journal}}: CS1 maint: multiple names: authors list (link)