Krapcho Decarbalkoxylation

A. P. Krapcho et al., Tetrahedron Letters 1967, 215.

The decarbalkoxylation of malonate esters, β-keto esters, α-cyano esters and α-sulfonyl esters in dipolar aprotic solvents, at high temperatures, in the presence of water and/or salt, to yield esters, ketones, nitriles and sulfonyl derivatives, respectively:



Scope and limitations: A. P. Krapcho et al., J. Org. Chem. 43, 138 (1978). Mechanistic studies: A. M. Bernard et al., Tetrahedron 46, 3929 (1990); P. J. Gilligan, P. J. Krenitsky, Tetrahedron Letters 35, 3441 (1994). Review of synthetic applications: A. P. Krapcho, Synthesis 1982, 805-822, 893-914.