An attractive reagent in organic synthesis due to its high acidity (pKa 4.97) and tendency to regenerate acetone. Applications include: an alternative for cyclic malonic esters; 1 formation of alkylidene derivatives as dienophiles in Diels-alder reactions and Michael acceptors; 2 efficient synthesis of 2-alkyl-4-pyrones3 and isofraxidin4; a reactant in Knoevenagel condensations that can be accelerated in ionic liquids.5
1. Tetrahedron 2007, 63, 389.
2. Monatsschr. Chemie 2003, 134, 1651.
3. Org. Synth. 2000, 77, 114.
4. Synth. Commun. 1993, 23, 1147.
5. Synth. Commun. 2006, 36, 3043.